


Challenge Accepted

by Shtwriter_yup_datsme



Series: Challenge Excepted Series [1]
Category: Supernatural
Genre: Alternate Universe- No Supernatural, Aromantic, Aromantic Gabriel (Supernatural), Canon Gay Relationship, Canon LGBTQ Male Character, Canon Lesbian Relationship, Castiel and Anna Milton are Siblings, Castiel and Lucifer (Supernatural) are Siblings, Charlie Bradbury & Dean Winchester Friendship, Destiel Week, Everyone Is Gay, F/F, F/M, Fluff and Mush, Gabriel (Supernatural) Has a Plan, Gabriel is a Novak (Supernatural), M/M, Minor Charlie Bradbury/Jo Harvelle, Non-Graphic Smut, Sabriel Week 2019, Trans Castiel (Supernatural), Trans Male Character, Young Castiel/Young Dean Winchester, Young Dean Winchester, Young Sam Winchester
Language: English
Status: Completed
Published: 2019-09-08
Updated: 2020-07-17
Packaged: 2020-10-12 12:42:36
Rating: Not Rated
Warnings: Underage
Chapters: 20
Words: 37,987
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20564519
Author URL: https://archiveofourown.org/users/Shtwriter_yup_datsme/pseuds/Shtwriter_yup_datsme
Summary: Gabriel Novak is hot, rich and Souix Falls resident Trickster, he's got with almost every single person at the school but when Sam Winchester shows up seeming somewhat immune to his devilish charms Gabriel makes it his mission to get Sam to fall for himWhatever it takes-There is an age gap between Sam and GabrielSam is 16 (almost 17) and Gabriel is 18 (almost 19)





	1. First Day

**Author's Note:**

> Sup this is my first fanfic book thing so I hope you guys enjoy, I might not post that frequently but I will try my best!

Sam stood outside of his new school 'Souix Falls High' looking at it through his camera before clicking the button and taking a shot of it 

His family had just moved a few days ago for no reason other than his dad saying that they 'Needed a change' though he called it bullshit but at least it got him away from his own problems 

He didn't like new places much, he didn't know anybody or have any friends which didn't really matter considering he was kind of a loner anyway even if his brother Dean thinks it's unhealthy 

Sam wandered the halls of his new school confused and slightly nervous since his brother had left him to head to his own class leaving Sam to find his way alone

Sam stood outside the door of his first class -english- taking in a shaky breath before placing his hand on the door handle, gently pushing it down and walking in

Luckily the teacher wasn't in the class yet so he quitely made his way to the first empty seat he saw and began to wait patiently, "Nice camera" The girl sitting next to him said and Sam's eyes looked to her, - she had bright curly red hair with bangs that almost covered her eyebrows and she happened to be wearing a shirt with a reference to one of Sam's favourite tv shows on it 

"You a photography major or something?" She asked and Sam shook his head "Nope, I just like to take pictures you know 'capture the moment' if you will" He joked and the girl flashed a smile "Maybe you could take a few pictures of me sometime" 

He nodded "I will definitely take you up on that sometime- I'm Sam" He said introducing himself, the girl smiled "I'm Charlie" She said and went back to tapping her pencil on her desk, She sighed and turned back to Sam "Hey you should totally come and hang with me and my friends at lunch later, we could always use a new face" She offered kindly

Sam frowned for a moment, was she trying to be friends with him? "Uh- yeah sure" He answered awkwardly though happy that he'd been invited to not have to sit alone at lunch even though he liked being alone anyway 

"Gabriel Novak, just because you're father may be a important person to this town does not mean that you can skip class" Their teacher said angrily as he entered the room holding a student by his jacket, Sam's eyes ran over the boy, his short height, his long-ish and messy honey blonde hair, his fit build and somewhat colorful choice of clothing- excessive Sam thought 

"I wasn't skipping- I told you I had a sick note" The boy Sam heard to be Gabriel defended lazily 

The teacher rolled his eyes "Take a seat Mr Novak" He said pushing Gabriel towards his desk, Gabriel sighed muttering something under his breath before taking his seat at the back of the class 

Sam shifted closer to Charlie "Hey what's his deal?" He whispered and Charlie leaned closer to him "Gabriel Novak-him and his family are every teachers worst nightmare, he's got like 10 other siblings but he is the worst out of all of them, he's bit of a trickster especially loving giving bullies their just desserts" She explained and Sam's eyes glanced towards Gabriel who was flirting with the girl sitting next to him, Charlie chuckled before adding "And he has slept with almost everybody here- you don't want to go down that road, trust me"

Sam's eyes widened "Oh god no-he seems like an ass anyway" He said and he meant it, dating was the last thing on his mind, Charlie raised a brow but sighed and looked back to the teacher "Okay"

~

Turns out Sam and Charlie had quite a few classes together so they were pretty much with each other all day, they spent most of he time getting to know one other and become quick friends since they had most of the same things incommon

They sat at Charlie's usual lunch table waiting for the rest of her friends who usually ran late 

"Sup nerds" A boy said as he sat down next to Charlie, the boy had messy dark brown hair, a few piercings on his face; bottom lip, nose and eyebrow slit, he wore a white tee with ripped black jeans that had a silver chain hanging from the side and Sam noticed he had on quite a lot of rings as well 

He was with another boy- one Sam recognised immediately "Hey Sammy" Dean said as he sat down 

"That's Sammy?" The boy asked Dean who nodded, the boy frowned and took a bite of his sour green apple "I thought he'd be younger" 

"It's Sam" Sam corrected throwing a look at Dean, "Why the hell are you here Dean?" Sam asked annoyedly 

"I'm not stalking you, Cas is in my science class" Dean said and Cas looked at Sam "Do you know your brother sucks at science?" Cas asked and Sam shrugged "Dean sucks at everything" 

Dean huffed "So I poured the wrong liquid into the tube, sue me!" Cas chuckled "You were so close to setting the place on fire dude" 

Deab rolled his eyes and pouted in his seat "Whatever" Charlie turned to Castiel "Cas remember Sam's new and I actually like him so please for the love of god go easy on him" She begged 

Cas raised a brow swallowing his apple "Why are you looking at me?, Gabriel's the devil incarnate" Sam frowned, Gabriel? As in the guy from his class? 

"Just make sure he doesn't to anything stupid okay?" Charlie asked but before Cas could answer Gabriel had walked up to their table and sat himself down "Who doesn't do anything stupid?" Gabriel said innocently 

Sam raised his brow at Charlie, she bit her lip "Oh yeah I might of forgot to mention that he's one of my best friends.." 

Sam rolled his eyes, Gabriel scoffed "Were you bad mouthing me again Charles?, seriously?!" 

"I wasn't bad mouthing you I was just warning him about you" She said "Sam actually seems like a decent person and I don't want you ruining him with your, Gabrielness" 

Gabriel smirked with a shrug "Hey I can't help it people love me" He sent a wink at Sam, Sam chuckled "Not even with a thousand condoms dude"

Gabriel paused for a moment blinking repeatedly "So there's a number?" Sam rolled his eyes again 

"Sorry about my brother he can be a pain in the ass all the time" Cas said "He's your brother?" Dean said incredulously, "You guys look nothing alike" 

"It's called adoption dumbass" Gabriel deadpaned "And I still wonder everyday why I got stuck with you as a brother" Cas smiled sarcastically and Gabriel flipped him off 

"What'd I miss losers?" A blonde haired girl asked sliding into the seat next to Charlie's, her eyes widened a bit as she looked around the table meeting Sam and Dean's equally shocked faces "Woah, blast from the past" She said breaking the ice 

"No way, Jo freakin Harvelle" Dean exclaimed "I haven't seen you since you were in pigtails" Sam laughed and Jo glared at him "Watch it Winchester" She muttered warningly "I thought your parents dragged your ass out of Kansas what the hell are you doing back?" 

Sam shrugged "Dad said we needed a change- though I bet you fifty bucks it was just so that he could dump us with Bobby when him and mom are working" 

"You know each other?" Castiel said getting them to acknowledge the rest of the group, "Cousins" Sam answered quickly "I can't belive you still live in Kansas, how's Ellen?" 

"Same old scary ass mom" Jo smiled "But eh, gotta love her" Jo turned to Gabriel "Oh and Gabe, that's my leg" She deadpaned referring to the fact that Gabriel had been stroking her leg under the table from the moment she sat down

Sam laughed "Nice try" Gabriel huffed frustratedly "Seriously?, you're telling me that you don't feel attracted to me in the slightest?" 

Sam shook his head "Nope" He smirked "I'm pretty sure you have about 3 different types of std's" 

Cas laughed and high fived Sam "Aw man we are definitely going to get along great" Cas exclaimed "I hate all of you" Gabriel said just as the bell rang 

"Welp I guess you'll just have to hate us all from gym class" Charlie muttered

~

"Bye guys" Dean waved off to his and Sam's newly made friends before hopping into baby; his 67 Chevy Impala, his one true love 

"So today went well" Dean said trying to make conversation "Yeah it did" Sam replied dryly 

"Sam are you doing okay?" Dean asked concerningly "It's just after- you know, you seem more.. closed off then usual" 

Sam sighed "We broke up Dean, I'm obviously not going to get over it in a week"

"Well.. yeah but she cheated on you, you shouldn't be so heartbroken over her" 

"We were dating for a year Dean of course I'm going to be heartbroken" Sam exclaimed annoyed by his brothers words "She didn't deserve you Sam" 

"Dean you don't get it you've never been in love" 

Dean paused for a moment "Okay yeah- maybe I don't but, I do know that when someone cheats on you that they don't love you" 

"Whatever- just drop it Dean"

~

Gabriel stalked drunkenly around his family's gigantic house almost as if he was in deep thought, his head turned vastly to the door as his younger brother Castiel walked in looking tired 

"I just had a 'lovely' chat with your latest hook-up.. he seemed overjoyed" Castiel muttered plopping himself down on the couch "Are you drinking dad's whiskey?" He asked pointing to the glass in his brother's hand 

"It's my after sex drink, you know that" Gabriel shrugged taking another sip "Why do you insist on sleeping around anyway?, It's not like you care for any of the people you sleep with" 

"I don't" Gabriel smirked and bit his lip "But sex is-.." He drew in a cold breath through his teeth letting his sentence hang in the air "-I mean it is somewhat for filling- and extremely fun"

"Yes I get that- but when are you ever going to stop making people think that they actually have chance with you?" 

Gabriel took a sip of his drink "Oh relax Cassie, it's not like I'm doing anyone harm.. I make it 100 percent clear to them, It's just sex- I'm not interested in anything more" He said and Castiel rolled his eyes 

Gabriel chuckled "Why so angry little bro?, it's not like you don't do the same thing" 

Castiel shifted uncomfortably "I used to do the same thing" It was true Castiel was as much of a slut as Gabriel is, sleeping with whatever girl or guy was willing, he still does go for casual hook ups from time to time but recently he had decided that he wanted to be in a real relationship with someone 

Gabriel gasped sarcastically "Oh!, yes I almost forgot- my dear brother has decided to try and find love in this cruel, cruel world" He laughed bitterly and sighed "I've been telling you Castiel love isn't real" 

"That's what you think Gabriel- but people are capable of falling in love- real love"

"Doubt it" 

"So what?, it's just going to be one hook-up after the next?, for the rest of your life?!" Cas shot back angrily "Love is real Gabriel- people are capable of falling in it-you're just too scared to even try" 

Gabriel winced and sat his drink down on the table "Watch yourself Cassie- my choice regarding my love life does not concern you, I have my own reasons for the way I am" 

Castiel sighed "Whatever Gabe- I heard you got detention again, what did you do this time?"

"I may have spray painted a dick on a bathroom wall?" They both laughed "You are so lucky that you haven't been expelled yet dude" Gabriel shrugged with a smirk "While we're on the topic of school, how well do you know that new kid Sam?" He asked "Like why is he so closed off?"

Cas raised his brow "I don't know Dean didn't really talk much about him"

"Who's Dean?" 

"Sam's brother you idiot- why do you care anyway?"

Gabriel chewed at his lip "..No reason" He muttered and Castiel scoffed as realisation hit him "You're actually trying to get in his pants?, good luck Gabe you're not going to get anywhere" 

Gabriel only sighed and grabbed another bottle of whiskey from his dad's stash and poured himself a drink "You're right Sam doesn't seem like the hit it and quit it type" 

"So you're not going to go after him?" Cas asked hoping his brother was backing down 

Gabriel chuckled darkly "Even better, I'm going to get him to fall in love with me" 

~


	2. A date?

**Summary for the Chapter:**

> Gabriel tries for a date with Sam

**Notes for the Chapter:**

> This a bit short btw

Cas' mouth hung open "What?, you can't be serious-you're the one who's been saying love isn't even real!" 

Gabriel shrugged lazily "To me it isn't but to Sam it just might be, and if I can get if to feel that way about me then..." He trailed off mysteriously 

"You've gone insane" 

Gabriel shook his head "No I haven't" 

"Yes you have, spray paint dicks on bathroom stalls and throw pies in people's faces-" 

"Oooh that's a good one-" 

"But toying with someone's feelings?, Gabriel that's low even for you"

Gabriel didn't falter "Relax Cassie it's just a little fun" 

-

Gabriel huffed annoyedly as he left his detention, it was his third one this week so he hadn't had anytime to woo Sam and the boy had been around for a few weeks now 

They weren't friends but they did hang around each other a lot because of Charlie and Cas so Gabriel did get to throw a flirty comment Sam's way every once in a while 

He stopped in his tracks with a frown as he heard soft music playing in one of the rooms down the hall, he followed the sound all the way to the half open door of the music room, staring into the room 

He saw Sam sitting peacefully on a stool with a ukulele in his hands strumming on it quietly

"I was scared of dentists and the dark, I was scared of pretty girls and starting conversations, all my friends are turning green, you're the magicians assistant in a dream" He hummed softly "Ohh, and they come unstuck, lady running down to the riptide taking away to the dark side I wanna be your left hand man, I love you when you're singing a song and I gotta lump in my throat 'cause you're gonna sing the words wrong" 

Gabriel knocked on the door finally making his presence known and Sam's eyes shot up through his light brown hair and Gabriel felt his heart skip a beat "What are you doing here?" Sam asked semi annoyedly, "I came from detention" Gabriel answered with a shrug

San scoffed "Obviously"

"-I heard you singing- I didn't know you play the ukulele"

Sam sighed and set the instrument down "Well now you do"

Gabriel ignored the cold shoulder and raised a brow "Why are you here after school anyway?" 

"This is the music room isn't it?" Sam retorted, Gabriel chuckled slightly at Sam's anger "Yes I can see that" He grinned and Sam looked up at him with a sigh giving up his tough act "I come here to play a few times a week-.. to clear my head" 

"Clear your head of what?" 

Sam ignored his question "Do you want something Gabriel?" 

Gabriel nodded, this was the perfect opportunity "Yes actually, I happen to have this extra movie ticket but I have nobody to give it too..mind taking it so you can go with me?" He smiled sheepishly 

Sam raised his eyebrows "...Are you asking me out?" He deadpaned 

"..No I'm giving you a free opportunity to go to the movies with me" 

Sam shrugged "..So a date?" 

Gabriel rolled his eyes "..Just go out with me" 

Sam laughed unimpressed by Gabriel's lame efforts "If you're trying to get in my pants you're going to have to try harder" 

"Come on Sam weve known each other for what three weeks now?, isn't it time we get together? 

"No" 

"I promise I'm not trying anything, I'm just simply asking you out"

"Okay...I'll consider it, if you answer one question for me" Sam said leaning on his knees "Go head" Gabriel smirked confidently 

"Why do you do it?" 

Gabriel frowned "Do what?"

"Act like a douche bag 24/7,sleep around and act like you're emotionless when it's obviously not who you are"

Gabriel was taken aback, not really knowing how to respond to that, Sam sighed and stood up picking up his ukulele and looking Gabriel in the eyes "If I did want to go out with you, which Gabriel would I be going out with?" 

~


	3. Get To Know Me

**Summary for the Chapter:**

> Sam and Dean head to the Novak residence for a nice pool day

"Sam come on we're going to be late let's go!" Dean yelled through the house for the second time; they were heading to the Novak's to hang out at their giant pool since it had been blazing hot for the past couple days 

"You just want to see your boyfriend Dean" Sam muttered stalking down the stairs and swinging his bag over his shoulder, their mom turned around instantly dropping the plate she was washing into the sink "Boyfriend?- what boyfriend?" 

Dean smacked Sam up the head "He's not my boyfriend!" Sam grinned "I swear I could've sawn you guys making out in the Impala the other day" He lied 

Their mom smiled "Dean?"

Dean scoffed "That never happned!" Sam shook his head "Denial, denial, denial" 

"Okay what about you and Gabriel?" 

"There is no me and Gabriel" Sam said way to quickly, their mom perked up "Who's Gabriel?" 

"Sorry mom were going to be late!-" Sam yelled turning to his lauging brother and pushing him towards the door 

~

The brothers stood staring at the large pool area, Charlie was sitting on the edge of the pool in her cute light yellow bikini laughing with Cas and Gabriel's younger sister Anna in her tanned pink two peace and Jo was racing two of the Novak brothers Lucifer and Balthazar across the big pool 

Cas was tanning with his shirt on and Gabriel was- were was Gabriel?, He wasn't at the pool which made Sam suspicious, he turned to Dean "Tell Cas I said hi I'll be right back" 

Dean grimaced at his brothers weirdness but ultimately shrugged it off, heading over to Cas who was sat on one of the pool chairs reading some book 

"Sup buddy" He greeted with a smile, Cas looked up from his book and immediately broke out into a grin "Dean you made it" He sat up and put the book down "Where's Sam?" 

"Don't know he ran off when we got here" 

Cas huffed hoping it didn’t have anything to do with his scheming brother, but before he could open his mouth a certain bouncy redhead ran up to them "Dean!" She exclaimed happily pulling him into a hug 

"Hey Charles"

"So now that you're here, what should we do first?- I was thinking splash challenge or- no that would never work" Dean frowned at Charlie's sudden rambling "What is she on about?" He whispered to Cas

Cas shrugged lazily and stood up grabbing a drink from the cooler "She does this all the time, you'll get used to it"

"Can you do a flip into the pool?" Charlie questioned Dean excitedly, "Yes I can" Dean nodded 

"Good- I need you get water on Anna" 

Dean raised a brow "Why exactly?"

"It's fun?" Charlie said unsure of her answer, "Meh good enough for me" Dean chuckled pulling his shirt off before running up to the edge of the pool and doing a flip right next to Anna causing the water to get all over her

When she got eyes on Dean as he swam to the edge of the pool she looked furious "Dean Winchester you are a dead man!" She scoffed and stood up running over to get her towel 

Cas and Charlie ran over to him "Do you actually think she'll try to kill me?" Dean asked sounding somewhat scared of Anna's threat

"I doubt it" 

"Definitely" Charlie said at the same time getting a bitchface from Dean before he grabbed her arm and pulled her into the water "Dean!" 

Him and Cas broke out laughing as the redhead swam back up to catch her breath "Fuck you- both" 

Dean grinned "Come on Cas get in" Cas shook his head "Sorry can't doctors orders" 

What does that mean?" Dean asked curiously, Cas ran his tounge over his bottom lip "...I had surgery last week" 

Charlie gasped, her anger gone "What you got it?!" Cas smiled happily nodding 

"Why didn’t you tell me sooner?!" 

Cas cleared his throat "It never really came up" Charlie bitchfaced him "Bullshit Novak" 

Dean coughed getting them to acknowledge him "Why are we so happy about Cas getting surgery?" 

Cas looked to him "Top surgery, I'm trans" 

-

Sam walked up the Novak's large stairs in search for Gabriel; He didn't even really know why the hell he cared, he didn't even like the guy but he carried on anyways 

He walked the long halls until he spotted the large door Anna had mentioned; it was way crazier than he had thought, it had a wooden sign placed right in the middle with the words 'The Trickster' plastered onto it and surrounding the sign was multiple colors, making Sam wonder if Gabriel had painted the door himself 

He sighed raising up his fisted hand and knocking on the door a few times, after a few seconds the door was opened and a paint covered Gabriel behind it "Samich?, we're making house calls now are we?" He smirked 

Sam rolled his eyes, typical Gabriel "No you dick, I just wanted to know why you weren't down at the pool" 

"Oh! yes that" He let Sam into the room and younger boys eyes scanned over it; the three bright yellow walls, the Queen sized bed with brown sheets that a large dog was currently sleeping on, the pansexual pride flag that hung above the headboard of his bed and the flat screen TV on one of his dressers that was currently playing the second episode of the first season of Shadowhunters 

Surprisingly the room was quite clean there weren't any clothes lying around or candy wrappers that had been tossed wherever, the only thing that really caught Sam's eye was what Gabriel was currently painting on the fourth wall 

It was beautiful, the way the blue, pink, and purple came together to color the sky and how the white clouds sat perfectly in the picture "You can paint?" Sam asked staring in awe at the wall

Gabriel shrugged staring at his masterpiece "You have your hobbies.." 

Sam faced him "Why are you painting on your wall?" 

"Have you met me?, I'm like the living definition of 'extra'" 

"Actually no I haven't met you" Sam said in a 'matter of fact' tone "You haven't exactly been forthcoming on that little topic"

Gabriel sighed; He'd been giving a lot of thought to what Sam had said in the music room the other week, he couldn't expect to make Sam fall for him without letting the boy know him "You're right, so what do you want to know?" Sam paused for moment "..You'll answer anything?" 

"Ask away Samshine" 

"Okay, how old are you?"

"18- almost 19" 

"When's your birthday?" 

"September 4th"

"Favourite food?" 

"Candy" 

"That's not a food" 

"It's edible" 

"Explain the dog" 

"His name's Dickie I got him for my 15th birthday" 

"Favourite band?" 

"It's a tie between Panic at the Disco and AC/DC" Gabriel grinned "..But that's not what you really want to know" 

Sam looked lost "What?" 

"If you want to know what I like just look around this room-" He shook his head "No, you want to know the personal stuff"

Sam rolled his eyes; Gabriel was right, everything Gabriel liked was in the room they were standing in at the moment, the band albums, the tv that was playing Shadowhunters, the candy wrappers stuffed in the bin- it was all there 

"Fine, you're right" Sam agreed finally "-Then tell me" 

Gabriel smiled softly "I'd love to.. on our first date" He proposed and Sam immediately shook his head "-No, hell no" He muttered as he started to leave 

"Fine, then I'll just let you spend the rest of your days wondering 'What was he going to tell me?'" Gabriel teased knowing it would get to Sam

Sam stopped just before he could leave room letting out an annoyed huff, turning around he put his finger up "One date" 

Gabriel smirked on the inside "I can't exactly tell you everything over one date" 

"Then fuck off" Sam spat going for the door "-Fine, I'll take it" Gabriel caved; It wasn't what he was hoping for but it was a start "I'll text you later" 

Sam squinted with a frown "You don't have my phone number" 

Gabriel laughed and dipped some paint onto his brush turning back to his art "Oh, trust me I do" 

\- 

Dean blinked "You're trans?" Cas nodded confidently "Yeah ftm, I have been since I was 4" 

"Why am I just finding out about this?" Dean asked curiously and Charlie smiled "See Cassie here isn't really a big sharer so don't take it personally" 

Dean huffed "Okay so if you can't come in the water what are we supposed to do?" He asked with a pout, thinking of fun Cas safe games they could play 

"Actually I've already got that figured out" Cas smirked and ran over to the edge of the pool coming back with a bucket filled to the brim with water balloons

Dean nodded impressed by Cas' quick thinking as he grabbed a balloon "I like your style Novak"

And then he threw it 

\- 

Sam walked out of the shower, drying his hair as he plotted revenge on his brother for hitting him with a water balloon

He sighed and grabbed a dry shirt from his wardrobe, fitting it over his head and flopping down onto his bed and checking his phone one last time before he turned to stare at the ceiling falling into deep thought 

He kept going back to his encounter with Gabriel earlier, -about the date- he kept telling himself that it wouldn't mean anything and that it was just to get information out of Gabriel and that was it

His parents always said it was his biggest problem, sticking his nose in other people's business, but he was just curious as to how Gabriel could be Gabriel, there wasn't anything more too it

Right?

-


	4. Date night jitters

**Summary for the Chapter:**

> Gabriel gets jittery about his date with Sam so he heads to a friends to help him cool off

Cas knocked on Gabriel's open bedroom door leaning on the frame "Hey"

Gabriel looked up from the dog he was petting "Hi"

"Why was Sam looking for you today?" Cas asked suspiciously, Gabriel frowned and stopped petting Dickie momentarily causing the dog to pout "How do you know that he was looking for me?" 

"Anna told me" 

Gabriel shrugged "He just wanted to know why I wasn't at the pool"

"Did you guys talk about anything else?" 

Gabriel shook his head "Nah not really, though I did ask him out-"

"You what?!" Cas exclaimed getting off the frame and stepping into the room "You what?" He said agian in a more hushed tone 

"I asked him out" Gabriel said more slowly "What did he say?" 

Gabriel grinned slightly "He said yes" 

"You're joking?" Gabriel didn't falter "-Why the hell would he do that?!" 

Gabriel sighed "I guess I'm just that good" Cas shook his head "No that's it I'm done with you- I'm telling Sam" 

"No meddling Castiel just let this play out besides why spend all your time invested in what I'm doing rather then in Dean Winchester?" He rasied his brows suggestively 

"What are you talking about?" Cas scoffed unconvincingly "Why your little crush- I mean I'm not judging you, if I weren't busy with Sam.." He left Cas to his imagination 

"Dean and I are just friends Gabe" 

"Suurrrreeee whatever you say Cassie" Gabriel chuckled and stood up grabbing his trainers from his shelf 

"Where are you going?" 

Gabriel shrugged lazily "For a run" 

"At 9:30pm?" Cas said incredulously, "I need to clear my head- don't wait up" Gabriel muttered shrugging on his open jacket and running out the room without another word

-

He made his stop at a house only a few blocks from his, he ran around the back and climed up the ladder that lead to a window 

He knocked twice and a the window was slid open by a girl with a smirk on her face; she had long-ish dark brown hair was wearing a black tank top that showed off her impressive chest 

Gabriel raised a brow "Let me in" She sighed and shrugged waving him in, and he climed through the small window

She sat on her blue bed "So what's up Novak?, you haven't come around in a while" Her and Gabriel have an on and off thing where they'd hang out, get drunk, smoke or sometimes have sex

They were friends but also fuck-buddies and for Gabriel this was one of those times, "Wait is this a booty call?" She asked with a laugh and Gabriel scoffed "No...maybe?"

"Well if it is at least tell me why" 

Gabriel sighed, she was always able to read him "..There's this guy okay" 

"You have a crush?!" 

"It's not a crush!- I'm just trying to sleep with him that's it..but I don't know lately I haven't been able to quit thinking about him, and now that we have this date coming up, I just can't help but feel a little jittery"

"Gabriel Novak jittery about a meaningless date?" She laughed "You like this boy!" 

Gabriel laughed loudly "Ha!- you almost got me there" 

Meg shook her head disprovingly and with a sigh pulled off her top "Okay" Gabriel frowned "Wait you actually want to?"

"Now that you're here don't leave me hanging" She crawled onto his lap and they engaged in sloppy kisses, his hands roaming her fit body as he found his way to her back to un-clip her bra letting it fall to the floor 

She pulled of his shirt and they scooted their way up the bed to continue their needy kisses, she reached down and slipped a hand in his shorts feeling up his hard on, he flipped them over so that she was on top and he pulled down and kicked away his shorts 

She grabbed a condom from the drawer and unwrapped the packet throwing it away, Gabriel scoffed "Oh come on you know I'm clean" 

She rolled the condom down onto his cock "Don't care, I'm not taking any chances" She took off her lace panties and slowly slid onto Gabriel's cock with a quite moan 

She placed her flat palms on his chest letting her brown hair fall in her face as she rode his dick, skin slapping gently as she did so 

"Agnh-" Gabriel grunted at the pleasure and his hips thrusting up for more, dropping her head back she moaned allowing her hips to grind faster 

She gasped in surprise as his hands slapped her ass leaving faint red marks, her orgasam was nearing

Gabriel wrapped his arms around her turning them over to that she was now on the bottom, her head fell onto the pillows and she moaned pornographically as he grabbed her hips and fucked into her hard and deep 

In a matter of minutes they both came, panting breathlessly Gabriel rolled off the condom and dumped it into the trash next to the bed "I think that was a decent fucking" 

-


	5. Date Night

Sam was running around his room looking for his text books; he was usually more organised but he was so tired after yesterday he had completely forgotten to pack them 

He was about to check his desk again when his phone pinged, he sighed and grabbed it off the bedside table

There was a text and Sam immediately knew who it was from 

From Anon- Sup Winchester (;

Sam rolled his eyes and changed the name in contacts 

Hi Gabriel 

From Jackass - You siked for our date this Friday?- you haven't forgotten have you?

Sam wished he had, he hasn't been able to stop thinking about there stupid date and why he had agreed to it 

From you -Sadly no 

From Jackass - Come on Winchester don't be like that you're making me sad :(

From You- Good

From Jackass - I'll see you at school- fyi Winchester words hurt

For some reason Sam smiled at that as he shoved his phone back in his pocket "What you smiling for?" Dean asked teasingly as he walked by Sam's room 

Sam's smiled faded "Nothing"

"What's this I hear about you going on a date with Gabriel?" Dean asked curiously as he watched Sam try to find his missing books

Sam swallowed "And where'd you hear that?" 

Dean ignored his question "Doesn't matter- I thought you didn't like the guy?" 

Sam grabbed his bag and started to stuff his books in it having finally found them "I don't"

"Then why are you going out with him?" 

Sam just rasied his brows and shoved past his brother running down the stairs and making sure that Dean heard the sound of the front door slamming as he did 

Dean scoffed and shook his head, he knew his brother was going through some stuff but why not talk to him? 

They always used to talk to each other about everything- things that were bothering them now Sam was just growing distant and Dean blamed it all on her 

She ruined him 

-

A slick back convertible drove up to the school stopping right in front of it, Meg turned to Gabe who was smiling down at his phone "You texting your guy?" 

Gabriel looked at her momentarily "Maybe" He shoved his shoved his phone in his pocket and grabbed his bag from the backseat "As always thank you for the ride Megan" 

"No problem Gabe" He kissed her on the cheek and pushed open the door and getting out but before he ran into the school, he leaned on her door "One more thing?" 

She dropped her sunglasses "Yeah?" 

"Do you know anything about dates?"

-

Unfortunately for Sam Friday came way too soon and so did his date with Gabriel 

It was around 6:43 pm and he was just about ready for the date he didn't even really want to go on, having settled with a red opened flannel that sat over a black tee and his most comfortable pair of jeans 

He looked pretty good- checking his phone for the time again, he looked in at the mirror one last time before he headed downstairs just as the sound of the doorbell rang through the house 

"Sammy! Your dates here!" Dean teased from downstairs "Shut up Jerk" 

"Bitch" 

"What are you doing tonight anyway?- gonna sit there on the couch eating popcorn and watching How I met your mother reruns?" 

"Yes" Dean answered like it was obvious, Sam rolled his eyes and pulled open the front door, and stared at Gabriel 

He was wearing tight black jeans and a rainbow tye dye hoodie with his hair- well there was glitter in it causing it to shine, but besides that he looked admittedly good

"You know there's glitter in your hair right?" Sam pointed out and Gabriel's expression went sheepish "There might have been a incident when pranking Castiel" 

Sam chuckled quietly, Gabriel smiled "A rose for my date" He said and gave a rose to Sam who tried to fight back a smile but failed "Thanks" 

Gabriel ran down the steps to his car and opened the door for Sam "Wow a real gentleman" He scoffed "Woah" 

"What?"

"This is your car?" Sam asked staring at the yellow lambourgini "Yes it is" Gabriel nodded watching while Sam admired his car 

"You do know that you're supposed to be on a date with me?-not my car"

Sam huffed "Fine- but you're letting me drive this at least once" Gabriel chuckled at him as they got into the car

"So Romeo where are we going?" 

Gabriel didn't answer he only looked at Sam and wiggled his eyebrows with his signature smirk before speeding off into the night 

-

They pulled up at a clearing in the woods, it was gave them a direct view of the moon and the twinkling stars; Sam thought it was beautiful

"What is this place?" He asked curiously, he'd been in the woods before to take some pictures with his camera but he'd never been this far 

Gabriel gave a small shrug "My own little spot" 

Sam looked outside the window "Lemme guess you bring all the girls here" 

Gabriel shook his head "I actually I've never brought anyone up here.. well except for you of course" He said truthfully; when he had asked Meg for advice she said not to go all out and be his usual crazy self but instead just ease into it with Sam if he really wanted to win the younger boy over, so he thought a nice stargazing would do the trick- a nice place where they could just talk 

It sounded boring yes but weirdly Gabriel thought it was something Sam might like and to be honest he liked the idea too "I found this place when we first moved here, I was bored and it was just here- so over the years I come here to clear my head" He explained

Sam was so shocked at the genuine tone in Gabriel's voice that he didn't know how to feel about it so he just tried to brush it off, Gabriel sighed; noticing Sam's reaction "You said you wanted to get to know me so, I'm letting you get to know me" 

"Okay-" Sam started but was immediately cut off "But first I have to get to know you, those are the rules"

Sam scoffed "No they're not!" He exclaimed incredulously and Gabriel nodded "Yes they are, so talk Sammy-boy" 

Sam huffed defeatedly "Fine what do you want to know?" 

Gabriel shrugged "I don't know maybe..why you're so closed off?" He said like he hadn't planned to ask the question 

But turns out he had unintentionally annoyed Sam "Why does everyone think that I'm closed off?" Sam said slightly angry, Gabriel rasied a brow "Who's everyone?" 

"You, Dean-my parents" Sam sighed "I- my I broke up with my girlfriend a few weeks before we moved here and maybe I'm still getting over her" He flinched at his sudden openness, he wasn't usually like that especially to a person he basically just met 

A girlfriend 

Gabriel thought to himself, that's why Sam is resisting him, he's still getting over someone which means his plan will probably take more time than he thought "Well if you loved her then it's gonna take some time to heal" He said gently 

"Yeah I did love her"

Gabriel shrugged "Well I wouldn't know how that feels" Sam frowned "What you've never had a girlfriend?" He questioned but then after Gabriel's silence he got what he had mean't "..You've never been in love" 

Gabriel shook his head slowly "Not once-..I mean it's not like I care, I prefer to be alone" He said "Since I was little I kinda always knew I didn't want somebody like that" 

Sam frowned "So you're aromantic?" Gabriel chuckled lightly at Sam's assumption "I guess I am kind of 'no romo'- I mean maybe one day I find someone who actually loves this" He gestured to himself 

"If you're not into relationships, then why are you here with me?" 

Gabriel exhaled loudly "I don't know, dates aren't actually my thing- well dates like this at least" 

Sam scoffed "You mean dates that don't end in sex?" 

Gabriel put a hand over his chest dramatically "Wait you mean we're not going to have sex?" He joked getting Sam to laugh slightly; he felt a warm feeling spred through his heart at the nice moment, it was weird he'd never been like this with anyone so open and like himself

\- 

All in all the date went surprising well, and Sam thought he might actually like Gabriel?

They spent the rest of the night joking and just talking about life and shit, it was nice- even better when they ended the evening with some icecream

After the candy boy dropped him off back home and Sam refused to kiss him causing Gabriel to drive away with a pout but leave Sam with a smile, he made his way inside quietly shutting the door not wanting to wake Dean 

Who was passed out on the couch with the tv still playing, Sam rolled his eyes at his brother and switched off the tv laying a blanket over him and cleaning up his mess before he ran up to his room to get some sleep

He changed out of his date outfit and set his alarm for the next day before finally going to sleep 

The only thing he dream't about, were those beautiful whiskey gold eyes...

-


	6. Surprise!

When Sam woke up it was to the smell of bacon..and pancakes and maybe eggs? 

It caused him to frown.; Dean would be too lazy to cook and their parents weren't getting back from their trip anytime soon so who in hell was making delicious food?

He stumbled out of bed and followed the delicious smell all the way downstairs and into the kitchen

He found a dark haired man standing over the stove happily humming as he flipped another pancake over and Dean was sitting at the table and waiting for his breakfast

Sam knew exactly who that man was 

"Michael!" He exclaimed running into the kitchen "Morning Sammy" Michael smiled, "What the hell?!- mom and dad never told me you were coming" Michael was their eldest brother, being 4 years older than Dean and 6 years older than Sam and he was kind of like the golden child

When he was 18 he left for college and they didn't see him for a while except for family holidays but they hadn't spoken to him since the move from Lawrence 

"That would be my fault" Dean raised his hand "I think I was supposed to tell you like..last week?" 

Sam rolled his eyes, of course his brother would forget "Why are you here?" He asked and Michael shrugged "Well mom asked me to check up on you guys and I was already in town so..." 

Dean scoffed "More like mom didn't trust me to take care of Sammy by myself" 

Michael waved the spatula "Well if you want to put it that way" Dean flipped him off "Wait what do you mean you were already in town?" Sam pipped up and Michael's face went crimson "I was visiting someone" 

"Who?" Sam and Dean both said in unison 

"A friend okay?" Michael muttered placing their breakfast plates on the table "A girlfriend?" Dean teased but Michael didn't falter until Sam spoke "Ooh a boyfriend?!" 

Michael sighed "Maybe, it's still new okay- just eat your breakfast" But sadly that wasn't the end of it, he was teased for the whole morning 

Ugh brothers 

\- 

Meanwhile Gabriel was having the best morning of his life; he stood in the long of hall of bedrooms clanging two pans together as he walked up and down the place "WAKEY WAKEY BITCHES!" He yelled repeatedly laughing to himself every few minutes 

"Oh my god Gabriel it's Saturday fuck off!!" Anna yelled from her room "You're gonna wake Hanna!" 

He opened her room door "She's at school so- WAKE UP!!!" He yelled again and Anna got up from her bed stomping over to the door and slamming it in his face 

He laughed; oh he loved torturing his siblings

After awhile Gabriel stopped with the noise and made breakfast which unsurprisingly got them to wake up so they were all currently sprawled out in the living room watching Pretty Little Liars 

"I bet you fifty bucks Lucas is A!" His younger brothers Alfie and Raphael challenged 

"I bet you 60 bucks that it's Melissa!" Anna said and Cas rolled his eyes "Guys it's obviously Walden" 

Gabriel scoffed, idiots he thought "I bet you all 100 bucks- it's ----" He said and they all laughed at him 

A few hours later 

"You have got to be kidding me" Cas gaped just as the last episode of season two ended, Gabriel was right it was ----

"Ha!- pay up bitches I want my money by tomorrow" He laughed manically like an evil king gripping the armrests of the couch like he was sitting on a throne 

Cas huffed "I hate you" Gabriel smiled back at him "I know you do"

"Gabriel!!!" A soft voice yelled from upstairs 

He sighed, it was his little sister Hanna; she just got out sick from school, he stood up from his couch to go check on her when the doorbell rang 

"Can one of you idiots get it- I have to check on Hanna" He asked stretching his back with a groan before running upstairs 

Alfie sighed and went to get the door when he realised that no one else was going to do it "Hi?" He said not knowing the people who had rang "Hi I'm Sam this is Dean- is Gabriel here?" 

Alfie shrugged "Come on in" He said letting them in the house, Sam gasped at the tv "Pretty Little Liars- oh cool did you guys find out that --- is 'A' yet?" 

Anna and Cas scowled "Sadly yes" He frowned at their grumpyness "Gabriel is upstairs second to last door on the left" Alfie told him and he thanked the younger boy before running up the stairs 

Dean smiled and sat down next to Cas "Hey buddy" He said gleefully and Cas pouted slumping in his seat "I just lost 100 bucks" 

\- 

Sam went to the door Alfie had described and found Gabriel; he was having a small argument with a child 

"Look Han you have to eat something" He said to the child "I don't want to" She sniffed like she had been crying

He hugged her "I don't like being sick" She cried into his shoulder "It's not all bad, you get to eat soup and watch tv and everyone has to be nice to you"

She laughed up at Gabriel and nodded "Okay I'll eat" She agreed and Gabriel sighed relieved "Thank you" 

Sam smiled without realising it; he didn’t know Gabriel was so good with kids, He finally knocked on the door "Hey Gabe" He whispered and Gabriel looked up at him from the bed 

"Samster how long have you been standing there?" He asked and Sam shrugged innocently "Long enough to see how good you are with kids" 

Hanna looked puzzled and nudged slightly at Gabriel's side "Hanna this is my friend Sam"   
  
She looked at Gabe "I like his hair it's pretty" Sam smiled at her sending a pointed look at Gabriel "Why thank you Hanna" 

Gabriel rolled his eyes and picked Hanna up propping her on his side "Walk Winchester" He said and Sam chuckled following him downstairs and into their large kitchen 

Gabriel set Hanna down and went to work on making her food "So Samich what's up?" Gabriel asked grabbing the store bought soup from the shelf 

Sam raised his brows "You don't remember?" Gabriel frowned "Remember what?" 

Sam pulled out his phone and read a aloud a text he got from Gabriel "Lunch, Roadhouse 2pm" 

"Ooooh yeah I forgot about that" He checked his watch "It's 2:45" 

Sam tucked his phone back into his pocket "I was busy" 

"Thinking about me?" Gabriel smirked earning him one of Sam's signature bitchfaces "No- actually my older brother us in town, we were hanging out" 

"Older brother?-I thought Dean was your older brother?" 

Sam rolled his eyes out of habit "He is doofus-I have another brother" 

"Huh- what's he like?- does he have your brown hair and weird eyes?"

"Weird eyes?" Sam repeated and Gabriel shrugged "You have like ten different eye colors- blue, green, gray, hazel, brown it's so hard to keep up"

Sam grinned "I didn't know you spent so much time staring at my eyes" 

"Not just your eyes.." Gabriel muttered under his breath "What?" 

Gabriel coughed "Hmm?- nothing, so back to this brother" He said changing the subject 

"Right-he's 22 just got out of college lives and somewhere in California- and for the record he has black hair and green eyes" Sam corrected him

Gabriel gaped "No frickin way" He laughed to himself as he shook his head "Gabe what?"

"By any chance is his name Michael?" Gabriel asked confidently and Sam was taken back "How did you know that?" 

Gabriel grinned mischievously "Because my dear Sammy boy, he's dating my brother, Lucifer"

"Come again?" 

Gabriel nodded "Yeah we all met him a few weeks ago- super nice dude I don't know how a guy that nice could get with Luci" 

Hanna smiled "He got me a lolipop, it was cherry, my favourite" Gabriel 'booped' her little nose as he put her bowl of soup on the table "Yes he did Han" 

"I am so gonna tease Mikey about this later" Sam grinned playfully, Gabriel clapped his hands "Okay, gimme a sec- I'm just gonna get changed real quick, can you watch over Han?" 

Sam nodded awkwardly "Sure" He agreed and Gabriel thanked him before running out the kitchen to get changed 

"Sam?" Hanna said looking up from her bowl of soup "Yeah?"

"Are you dating Gabbie?" She asked using the silly nickname she had for her older brother 

Sam almost choked on the air "Huh?- no, we've only been on one date, we're just friends- kind of at least" He tried to explain as best he could "Do you like- like him?" She said 

Sam shrugged sighing as he crossed his arms over his chest "I don't know Hanna" 

\- 

Gabriel ran down the stairs "Okay I'm ready" He announced staring at an annoyed group of teens "30 fucking minutes" Cas spat angrily 

"What I couldn't decide what to wear- don't judge" He muttered the last bit under his breath, "We're taking your car by the way" Cas informed him 

"What?- why?" 

Cas shrugged opening the door "Because" Gabriel rolled his eyes and grabbed his keys from the small bowl on the table before following the group outside 

"Hey Dean" Gabriel threw the keys to him "You wanna drive?" 

"Seriously?" Dean asked incredulously and Gabriel nodded knowing the other boys love of cars, Dean smiled and got in the drivers seat taking a moment to appreciate the car

"Are you fucking kidding me?- you won't even let me drive your car- why does Dean get to drive?" Cas complained, Gabriel looked back at him from the passenger's seat and smirked "Because" 

Sam laughed quietly before he was given the death stare from Cas and immediately shut up 

"Aww dude you have AC/DC?" Dean asked looking through Gabriel's songs "Hells yeah" Gabriel confirmed "It's like the only thing I listen to- well that and Panic"

Dean grinned inwardly, choosing 'Back in Black' before starting up the car, Gabriel nodded in approval "Nice choice" 

Sam watched them fawn over the song and smiled "You guys should be bestfriend's" He muttered and surprisingly Dean agreed with him "Yes, yes we should- you are much more fun than Sam" 

Sam felt slightly offended at Dean's comment but brushed it off "Heads up Dean- I got Cas to invite Micheal and Lucifer" 

"Why?" 

"Because they're doing it" Gabriel said in answer to Dean's question "-What?" Dean stuttered 

"Yeah they're dating" Gabriel repeated casually as if it was no big woop, Dean looked at Sam through the rear view mirror "Sam?!" 

\- 

They all entered the Roadhouse and headed over to where Michael and Lucifer were sat waiting and when Michael caught sight of his brothers walking towards them he immediately hid his face in the table 

"Fuck" He muttered into the table and Lucifer frowned "What- what is it?"

Sam smiled mischievously sliding into a seat "Sup love birds" 

Lucifer frowned "Who the hell are you?" Michael groaned "He's my brother" 

"And he's with us" Cas sat down along with Dean and Gabriel, "So I hear you're the guy who's dating my brother huh?" Dean introduced looking Lucifer up and down with a look of disapproval 

"Yeah- Lucifer" Lucifer held a hand out and Dean suspiciously shook it 

"So Luce, what exactly are your intentions with my brother?" He questioned letting his arm rest on the table leaning in closely to Lucifer 

Lucifer shifted uncomfortably, "Um what?" 

"You know, marriage- kids?" Dean continued, Michael gaped and slapped a hand over his face shaking his head softly, "Uh we just started dating" Lucifer muttered 

"So you don't plan on getting serious?!" Dean exclaimed "Sorry Mikey but as fine as your man meat is I just don't think he's the one for you" He deducted and the rest of the table laughed quietly 

Michael groaned "Oh my god" 

Lucifer shook his head "No- I do plan on getting serious it's just this whole relationship thing is new for both of us so we're just taking it slow for now"

Sam squinted; Lucifer really sounded genuine- it even surprised Michael a bit, Sam nodded "Okay he checks out" 

After getting over the fact that his brothers had no boundaries the group had a fun time getting to know each other better as they sat and talked for hours until finally it was time to go home 

They drove back to the Novak's in Gabriel's car and Sam, Dean and Michael got into the Impala

Gabriel was lean't on the open window of the passengers side "Sammy I'll see you tomorrow?" Gabriel asked and Dean rasied a brow curiously "What's tomorrow?" 

"I promised to help him take some pictures for his art class" Sam answered and Gabriel nodded "Yep it's going to be awesome" 

Sam scoffed "You're such a dork" 

"Aww but you love it" Gabriel sent a wink at him "See you tomorrow" 

Sam waved him off as they drove away back home and Dean shot a look at Michael before saying "So you and Gabe are getting pretty close huh?" He started 

"Dean for your sake I highly suggest you stop speaking" 

\- 

Sam was about to get dinner started when there was a soft knock at the door, he was chopping onions so he called for Dean get it but his brother never did so he was forced to pause his cooking and get it himself 

Cleaning off his hands he ran up to the door with a friendly smile "Hey-..Jess" His smile was completely gone, being replaced by a look that would make someone think he'd seen a ghost 

"Hey Sam"

-

**Notes for the Chapter:**

> Cliffhanger Bitches!
> 
> I didn’t actually think I was going to do Michifer and it was kind of a spur of the moment thing but I hope you guys liked it! 
> 
> Also the reason I put ---- at the Pretty Little Liars part was because I didn't want to give any spoilers away for any of you people who want to watch 
> 
> Anyways Ciao for now 🌈


	7. Jess

Sam had gotten ready early in the afternoon and headed over to The Novak's to help Gabriel with his project like he had promised

The encounter with Jess still bothered him but he decided to ignore it for the moment and focus on something else- hence throwing himself into Gabriel's crazy

He was leaning on Gabriel's yellow car, camera hanging from the strap on his neck as he waited for Gabriel and Cas to show up 

It didn't take long for the brothers to run out of the house, Gabriel shouting some curse word at one of his siblings before slamming shut the door

Sam's jaw dropped when he saw them  
"Woah what the hell happened to you guys' hair?" He held back a snicker as he pointed at the brothers' new hairstyles; Gabriel had a soft light golden pink- almost peach hair opposed to his natural golden caramel and Cas was sporting black hair with blue tips

Sometimes he wondered how the two were even siblings, Cas almost always wore black and if not that at least some dark color, and Gabriel on the other had the most bright and eccentric outfits ever- makeup and earings the whole nine

Though he looked fairly normal today, wearing just a white hoodie and denim jeans along with Cas in his black and white striped tee and tight black jeans

They were complete opposite

Sam shook himself from his thoughts, Gabriel shrugged "We thought it'd be fun" Cas smiled "And we were right" He fist bumped Gabriel as they all got into the car

"Cas how are you not cold?" Sam frowned, it was freezing in Souix Falls

Cas shrugged "Perks of being emo I  
guess" Sam huffed a laugh "I will never understand you" He turned to Gabriel "So Princess Bubblegum where to?" Sam grinned at his own joke and Cas laughed from the back seat

Gabriel scoffed "Laugh it up Winchester- but you know I look good" He smiled "Besides it fits my colorful aesthetic"

Sam didn't protest there; he kinda did look good. Cas looked up from his phone "Okay- Gabe Dean's at the auto shop so you can drop me off there" Cas told him "I still can't belive he works on weekends"

Sam snickered queitly "Yeah it's because he wants to- cars are his friggin life, he loves it there"

Gabriel rasied his brows "Enough to work on weekends?"

-

"I still can't belive you made us stop for popsicles Gabe" Sam complained as he ate his apple one; after they had dropped Cas off Gabriel had spotted and icecream truck and just 'had to get one' as he said

Gabriel smiled like a child "And I'll never regret it"

Sam scoffed rolling his eyes before the fell on Gabriel fitting his entire popsicle in his mouth like it was nothing, his mouth widening slightly as he stared, Gabriel chuckled pulling the treat from his mouth licking the tip seductively as he did so "Trust me Samich I've taken bigger"

Sam shook his head not letting Gabriel get to him "So what you're a bottom?" He retorted and Gabriel was slightly taken back "I can accommodate to either Samsquatch" He smirked playfully and Sam rolled his eyes though Gabriel could see a hint of a smile on his face

"Whatever" Sam muttered as they continued on their trail stopping to take pictures every time Gabriel saw something that caught his eye, they didn't speak much and Gabriel thought it was kind of strange but tried not to comment on it...until he couldn't

"You're very quiet"

"Sorry- I've just got something on my mind"

Gabriel frowned "Like?"

Sam sighed; he might as well tell someone "..You know that ex I told you about?"

"The one that cheated on you?"

Sam nodded; a little surprised that Gabriel had remembered "Yeah well apparently she's in town- came by my house last night"

Gabriel immediately thought that was weird "What is she stalking you?" He asked trying not to sound jealous

Sam shook his head "No, she said she has some family here or something"

"Well what did you say to her?"

-

"Hey Sam" Her soft voice said awkwardly "You look good, I feel like I haven't seen you in forever"

Sam swallowed; he felt frozen unable to move as he stared his past in face, so many emotions hitting him and once- anger- sadness even happiness

"Sam?" She said and he blinked "What are you doing here Jess?" He asked getting straight to the point not interested in small talk

She rubbed her neck shyly "My parents are away for a few weeks so and I have some family here that I have to stay with" She gulped "I heard you guys moved here- I wanted to see if that was true"

"Well now you know it is" Sam said bitterly, she sighed "Listen Sam-"

"I don't have anything to say to you" He stopped her; he didn't need a repeat of what happened last year "Goodnight Jessica" He said and closed the door in her face

-

Sam broke from the memory "Nothing really, I wasn't in the mood for her lies"

"Well good for you Sammy, once a cheater always a cheater" Gabriel sighed "Okay this is depressing- gimme your camera"

Sam shielded it away from him "Why?"

"My stupid project is about art and doing something out of my comfort zone or whatever- and I've painted trees and sunsets before I need something I've never done"

Sam raised a brow "And that is?.." Gabriel held a hand out for Sam to give him the camera and Sam reluctantly did

Gabriel smiled mischievously at him "I have never painted a person before"

Sam didn't get it for a second before he did and shook his head vigorously "Oh hell no!" He reached for his camera back but Gabriel wouldn't give it "Gabriel you are not painting me!"

"Why?-I could paint a moose in his natural habitat" Gabriel chuckled taking a shot of Sam's angry face "No Gabe I'm serious!"

"C'mon I'll even show to you before I hand it in- don't you trust me?"

Sam would've said 'no' right off the bat but he somehow found himself agreeing "Fine- but I'm not posing for your stupid picture- and I'll need my camera back when you're done"

"Deal and Deal" Gabriel nodded excitedly "Besides getting a picture of you isn't going to be that hard- well once I get you to smile, why do you hate doing that?"

"I smile all the time"

Gabriel broke out into loud laughter "Yeah- and I hate candy"

Sam rolled his eyes "Shut up"

"Okay okay I'm sorry-" He leaned in close and Sam felt his breath hitch "But just for the record you have a beautiful smile Samshine" and just when Sam thought Gabriel was going to kiss him the boy just smirked and continued walking around the woods and Sam had to run to catch up with him

-

Dean was rolled under a car working on his 2nd car for the day when Cas walked into the shop running around back to where he knew Dean worked

He called for Dean a few times but the boy couldn't hear him due to the earphones he was wearing "Dean!" Cas yelled again but Dean still didn't react until Cas kicked him in the shin

He rolled down from under the car "Ow what the hell!" He frowned and pulled out his earphones when he saw Cas' angry face staring down at him "Cas?- when did you get here?"

"Like 10 minutes ago"

"Why didn't you tell me?"

Cas scoffed "You're kidding right?- I yelled your name like 100 times

"Oh- sorry earphones"

"It's cool" Cas shrugged "Also- there's this girl waiting for you outside, she says she knows you?"

Dean stood up brushing himself off "What's her name?"

"Uh..Jess? I think" He watched Dean visibly flinch, going still "Shit" He sighed

Cas frowned confused "What?- who the hell is she?"

Dean shook his head "No one just some girl from back home?"

"Is she an ex?" Castiel asked afraid of the answer; he thinks he has feelings for Dean and it wouldn't help if some ex-girlfriend came to win him back

"Not my ex- Sam's, the one that broke his heart" Dean sighed "I have no idea why the fuck she's here, but I want her gone" He headed for the door but Cas stopped him "What are you gonna say?"

"I'm gonna tell her to leave or stay away from Sam at least!" He exclaimed angrily "She ruined him!- he used to be happy but now he's just distant and cold" He growled quietly "Because of her"

Cas huffed "Okay fine you can talk to her- but don't yell" He stepped out of the way and let Dean pass

Jess smiled when she caught sight of him coming towards her "Hi Dean"

Dean took a calming breath "I promised somebody I wouldn't yell- so what do you want?"

She huffed giving up her act "I want to talk to Sam but he won't return any of my calls and when I went to see him last night he-"

"You saw him last night?" He whisper-yelled "Yeah- didn't he tell you?"

Dean rolled his eyes "No" He muttered; of course Sam didn't tell him "Look Jess you've hurt him enough- he loved you and you used that to ruin him, so please..just go back home- or just leave Sam alone at least- he doesn't need you to hurt him again"

-

"Samich! Hurry up!" Gabriel yelled staring up at the sky- taking in the sunset he almost didn't notice when Sam ran up to him panting to catch his breath "Damn- you, you run fast"

Gabriel frowned; he hadn't even broken a sweat "I thought you were the rabbit?"

Sam clutched his chest "It's not my fault that you run like The Flash"

Gabriel scoffed shaking his head disappointed "Weak" He muttered "Anyway!- once you're done catching your breath *cough* weak *cough*, look up idiot!"

Sam huffed and looked up with a gasp, "Woah that looks...beautiful" He smiled up at the sight and Gabriel managed to sneak a photo of both of them in front of the sunset

"Gabe!"

"What?!- I'm capturing memories!"

Sam chuckled softly "Okay fine- you're off the hook this time" Gabriel smiled back at him and before they both knew it Gabriel was slowly leaning in

He dropped the camera from his hands to hang from the strap on his neck, his hands wrapped around Sam's neck and Sam didn't stop him, his breath caught in his throat and he leaned in as well, his nose brushing against Gabe's

Usually Gabriel was more confident and less scared but the thought of kissing Sam made him more nervous than he had ever been- he didn't want it to be too fast, rough, or rushed- it, it had to be perfect

But he didn't even have time to think when he finally realised that Sam's lips were on his, Sam's hands cupped his face in their plams

The first kiss was soft and gentle both of them were taking it slow learning each others movements and tastes -Gabriel tasted like his raspberry popsicle and Sam like his apple one- it was a few seconds before they took it up a notch- the kisses getting deeper and more needy

Gabriel's hands fell to Sam's waist pulling him closer and Sam's hands dug into Gabriel newly dyed hair, Gabriel smiled at the touch, smiling against Sam's lips before they both pulled away, lingering close for a few seconds, Sam swallowed trying to control his breathing "Whoa"

Gabriel nodded lightly "Yeah" Was all he could say, then Sam's phone began to ring- he jumped away from Gabriel -startled by the sound- staring almost awkwardly at Gabriel before answering "Hey Dean- wh-what is it?" He asked still trying to keep his breathing steady

"Did you know Jess is in town?" He sounded angry, Sam nodded "Yeah she came by last night- why?"

"She just came by the shop"

"What?!"

"Yeah, what the hell did you say to her man?"

"Nothing!- look I'm headed home now, we'll talk about it later" He heard Dean muttered something but didn't ask what it was, instead he turned off the phone and looked up at Gabriel "We should get back"

Gabriel nodded awkwardly "Yeah let's go"

-

New chapter that took weeks to make nothing new there

If y'all want to see how Dean, Cas, Gabriel and Sam look check out this same chapter on my wattpad @Shtwriter_yup_datsme 


	8. Halloween

**Notes for the Chapter:**

> This is kind of just a filler chap for Halloween so enjoy!

Ugh it was Halloween, Sam's least favourite day of the year, normally he'd ignore all the parties and dress up but apparently at Souix Falls high it was mandatory to come in costume on Halloween 

Which meant everyone was excited about it but him 

He sighed as he walked into school -in costume- and up to his group of friends who were all happily chatting 

Charlie was Hermirone Granger, Jo was Gwen Stacy -spider girl- Meg, one of Cas and Gabriel's friends had dyed her hair blond and gone as harlequin from Suicide Squad and Gabriel was- The mad hatter? 

He had on the big hat over his pink hair, no white face paint just light red eyeshadow, and the rest of the mad hatters crazy clothes, and surprisingly he looked pretty good 

"Sammy!- you came I half thought you were gonna bail" Gabriel smiled; he knew of Sam's dislike of Halloween so he didn’t expect him to show 

Sam nodded "Yup" 

"Who are you supposed to be?" Charlie asked waving her wand in the air "Well Hermirone..if you must know" He gestured slightly to himself, he was wearing one of Dean's white football jerseys -7 Winchester- with the shoulder pads and everything including white shorts with knee pads and black lines on his face -two on each side-

"I'm the average jock stereotype- or you know Dean" They laughed "Where is Dean?" Jo frowned and just then the boy came into the frame startling them, with hair from the 90s and fake blood on the corner of his white tee and little bit on his denim jeans 

"Hey!"

Gabriel nodded knowing exactly who Dean was "Billy Loomis, nice choice" 

Sam just shook his head and rolled his eyes "Who's Sam supposed to be?" He asked and Sam smiled sarcastically "You"

All of a sudden the lights went out and every student in the hall gasped, there was a loud scream and the karaoke version 'Victorious' by Panic at the Disco started playing and there was a spotlight on one person holding a mic as they walked down the halls singing amazingly 

Everyone and teachers watched the great performance cheering him on till the end and clapped as the lights came back on "Hey losers" Cas grinned; he was in a white dress shirt, black jeans and a black blazer 

"Lemme guess..you're Brendon Urie?" Charlie said and Cas gasped dramatically "How'd you know?!" 

"Was that you're actual voice?" Dean asked still shocked by the performance and Cas nodded "Down to the last second" He looked at Gabriel "Suck it" 

Gabriel rolled his eyes "We get it you can sing a bit better than me" He scoffed "Dick" Cas smiled proud 

"You guys are coming to our Halloween party right?" Gabriel asked "You're throwing a party?" Sam frowned

"Hells yeah- we do every year- we throw the best parties" 

Jo nodded "He's not kidding Novak parties are the best parties" 

\- 

More like Novak parties are the biggest parties

Sam thought, thinking back to what Jo had said, he stalked around large house after turning down the 3rd drunk girl that hit on him, he opened another door looking for Dean or Cas or someone he actually knew but the only people there were some random people making out in the upstairs closet 

He sighed and walked along the large hall opening another door he found a drunk Dean going down on some girl and he didn't even notice that Sam had opened the door but then quickly slammed it closed "Oh fuck no" He muttered- eyes wide 

"You okay Samich?" Gabriel asked walking up the stairs and Sam huffed "Yeah I'm fine" 

Gabriel noticed the tiredness in his voice "Come on let's go somewhere more quiet" Gabriel said leading them to his room an locking the door so they wouldn't be interupted "What's going on?" 

Sam sat on the bed "Nothing...I just, Halloween isn't really my thing'" 

"C'mon!- Halloween is awesome, the candy, the costumes the gore" Gabriel exclaimed, Sam chuckled softly "Yeah I used to think that too-.. you know, when I was seven I dressed up like batman and Dean told me I could fly so I jumped off of our shed and broke my arm" 

Gabriel laughed "Oh my god really?!" Sam nodded "Yeah.." 

"So is that why you hate Halloween?'" 

Sam shook his hesd "No..that's another story" 

"Then tell me" 

Sam sighed "It's embarrassing" Gabriel shrugged popping a loli in his mouth "Even better" 

"Nah.." 

"Please!- what if I share a secret of my own" 

Sam squinted "Go on.." 

"No one really knows this but..my name isn't actually Gabriel"

Sam furrowed his eyebrows   
"What?" 

"Gabriel is my middle name, I was actually named after my grandfather..uh..Richard" 

Sam smiled holding in a small laugh "You're name's Richard?"

He gave a small nod "My mom was the only perosn who called me 'Gabe' when I was little and I liked it, so I stuck with Gabriel"

"..Okay" With a sigh he began his story "I was 13 and had a huge crush on this girl Andrea and she was throwing a Halloween party, so obviously I went..we played to some games and then- bobbing for apples.." He winced "I had been nervous the whole time because I really liked her so my stomach was... then when it was my turn...I.."

Gabriel's eyes widened slightly "Don't tell me you...?" 

"I threw up- breakfast, lunch, dinner, all of it just came out- mostly on Andrea- I was so embarrassed I ran out into the woods until Dean came and found me" 

Gabriel laughed "That's why you hate Halloween?- because you puked on some chick?!" He shook his head "No that's not exceptabe- next year we're going all out.. screw some huge party, just us- and I guess our friends can come too or whatever- but I promise you Sam Winchester you are going to have the best Halloween of your life" 

Sam smiled sheepishly at him "Thanks...Richard" 

Gabriel's smiled faded "Seriously- I'm trying to be nice and you have to pull that?" 

Sam snickered "Sorry I had to- I promise I'll never call you that again" 

"Good"

"Unless I'm mad at you" He added quickly, and Gabriel flipped him off standing up from his chair "I'm gonna change gimme a sec" He muttered and ran into the bathroom coming out in a soft pink hoodie and white pajama shorts, he switched on the tv and got into bed with Sam patting he bed lightly "Come on" 

"What?" 

"Those idiots aren't gonna leave anytime soon and I have a ton of snacks hidden in here- so let's wait it out"

Sam smiled a little "Okay" He said cuddling up with Gabriel "Have you ever watched Scream?" Gabriel asked grabbing the remote 

"Just the first one" 

"Then you are in for a treat Winchester" 

They managed to watch 3 movies without falling asleep, and between all of Gabriel's yelling at the tv and obnoxiously loud chewing to piss Sam off, he had a really great time with Gabriel

The best part of the night was when he fell asleep in the older boys arms breathing softly into his hoodie 

It was definitely a Halloween to remember 

-

**Notes for the Chapter:**

> I did it- I actually fucking did it!- I wrote a Halloween chapter in three hours with time to spare 
> 
> I need a fucking award 
> 
> Anyways I hope you all have/had a lovely Halloween 
> 
> Ciao!💀♥♥


	9. Awkward

One day before Halloween 

-

Gabriel spent most of his night thinking about the kiss he had shared with Sam, it was more romantic then sexual and it made him feel vulnerable- almost weird even, especially when his heart started to speed up just at the touch of the boy 

He wanted so badly to hate it but he couldn't- he was so torn by it he didn’t even feel like bragging about it Cas 

He had to figure his feelings out on his own 

After dropping Sam off with Dean and Cas he drove himself home, not trusting himself to be around Sam for any longer 

He wondered what the kiss had mean't to Sam- if it did mean anything 

Could've just been using Gabriel as a distraction from his Jess drama-not that Gabriel could be angry about that, he was trying to manipulate Sam into sex- which was admittedly worse 

It was about 7pm when he got home after making stop for a pack of cigarettes and some snacks, he headed inside setting his things down on the table by the door, he found his siblings huddled up in the living room watching tv 

He tapped Anna on the shoulder and she pulled down her headphones, "Oh you're back" 

Gabriel nodded "Has Han eaten yet?" 

"Yeah I fed her about an hour ago- showered too" He quitely thanked her and went to pick up their little sister from the floor "Gabby!" She laughed 

"Bedtime missy" He said and she shook her head "I'm not tired" She tried with a yawn and Gabriel chuckled to himself "Han you have to go to sleep" 

"Why?" She whined and Gabriel sighed walking them over to grab his things from the door and head upstairs "Because so you can big and strong like superwoman!" He spun her around and she giggled "All superheros need sleep" He entered her room and placed her on the bed 

"Okay" She yawned, he smiled gratefully and picked a small piece of candy out of his bag giving it to her she smiled "Don't tell your sister" He said, knowing Anna's dislike of his sugary ways 

He tucked her in "Lights out missy, I'll be checking on you soon" 

"G'night G-Gabby" 

Gabriel flipped on the lamp by her bedside and left the room to his own, Dickie sat up almost instantly, strutting over from his little dog bed to nuzzle at Gabriel's leg 

"Hey buddy" He huffed a small smile bending down to pet him, the dog let out a pleased sound and leaned into Gabriel's touch 

He stood up and let out a long breath "Fuck" He muttered, throwing his stuff on to the bed he changed into some more comfortable clothes and reached into the bag for the pack of cigs he had bought and a beer 

He walked over to the his window pulling it open he sat on the ledge lighting his cigarette, he rested his head on the wall as he stared out the window, there was only one person he was thinking of 

Sam

Why was he so caught up on Sam?- everything thing about the boy made his heart want to jump out of his chest 

His smile, his kaleidoscope eyes- that sweet laugh, Gabriel couldn't get enough of it, he sighed blowing the smoke out the window, his unwanted thoughts were cut short by the sound of his phone ringing- but not the one in his pocket 

His work phone, he hopped off the ledge to answer it "Dad?" 

"Hey Gabe- just calling to make sure you've looked at those documents I sent you" 

Documents?- Gabriel thought for a moment before he froze remembering that his dad has sent him some papers to look over before his meeting- he was supposed to get them done but forgot 

"Shit" He muttered "Yeah, the documents, I'm almost done- I'll update you tomorrow" 

"Great- how's everything back home, your mom and I miss you guys" 

Gabriel smiled "We're fine as always no one has burnt the house down yet- so there's that" 

"And you?- how are you Gabe?" 

"I'm good- taking my meds and keeping my nose clean-ish, just a few more months til college" 

"That's good- take care of yourself Gabriel- tell the other rugrats we love you and we'll be home soon" Chuck laughed "I gotta go your mom just saw some macaroons 

"Bring me back some!" 

"Yeah yeah" 

His dad hung up, Gabriel went straight to work on the documents he forgot to look over, popping open the can of Monster he bought 

It was going to be a long night 

\- 

After Halloween 

-

Sam was looking forward to the next day at school-hoping to talk to Gabriel since they didn't do much of that in the car, and on Halloween they had agreed to put any talk of the kiss they shared on hold, not wanting to ruin the day

But when he got to school it was like the boy was avoiding him, even in the classes they shared together Gabriel was avoiding him and he couldn’t figure out why

It wasn't until the first lunch break he decided to do something about it, walking up to Cas who was stood by his locker probably waiting for Dean 

"Hey Cas do you know where Gabriel is?- he's been avoiding me like all day" 

Cas shrugged "Probably having lunch outside- though I wouldn't call it lunch, what happened with you two by the way?- he was super quite when I got home two nights ago" 

Sam frowned in surprise "He was?" 

"Yeah I've never seen him like that it was super weird" 

Sam flushed "Well we may have..kissed that day, probably freaked him out or something" 

Kissed? 

Cas was utterly confused, he thought Gabriel would have bragged about kissing Sam all morning- what the hell was going on? 

"...Check behind the school, he goes there to be alone a lot, good luck" He said "And Sam?"

"Hmm?" 

"Be careful, Gabriel isn't someone to get involved with feelings and I don't want you to get hurt"

Sam nodded "Thanks, but I think I can take care of myself" He waved Cas off and headed outside 

Castiel sighed, I hope so Sam..I hope so 

-

Gabriel sighed dropping the can of spray paint on the groud he lean't on the wall behind the school, lighting his cigarette before taking a puff; it felt so good, he didn't smoke often but when he did it was like he was on cloud 9, it made all his problems go away just like that, and he could say with 100% certainty that it the feeling of lighting one was way better then any orgasam sex could give him 

He smoked when he was depressed, he smoked before coming out to his family, he smoked after the thing with Anna and it's probably the reason he's still standing, if not for the little cigarette packs he buys at the convenient store for 1.99, there's a good chance he'd be dead 

He knew he'd been avoiding Sam all day, but he couldn't face the kid- not in his state..not yet

"Really?-you smoke?" Gabriel pulled the cigarette from his lips as a smirk grew at the voice, he put the cigarette out and turned to the boy with a smile "Yeah, got a problem?" He feigned his usual confidence though mentally cursing at Castiel for telling Sam where he was 

Sam didn't respond he only shook his head disprovingly and lean't on the wall next to Gabriel, "I don't do it all the time- it just helps me, relax" 

"What- sex doesn't ?" 

"Is that a hint of jealousy I detect in your voice Sammy boy?" He teased with a light laugh, "No" Sam muttered weakly 

"Well if you must know, sex doesn't compare to the feeling of a cigarette against my lips- I mean it's all just meaningless anyway" 

Sam frowned "All of it?" Gabriel could of sworn he heard dissapointment in the young boys voice but he didn't bring it up only confirmed Sam's thoughts "All of it- unless you're special of course" He added and Sam perked up a bit "Special?- what does that mean?" 

Gabriel shook his head, he wasn't about ready to let Sam completely in "Nothing- why are you here anyways Samich?" He asked changing the subject and lighting another cigarette 

"I wanted see how you were doing- that's what friends do" 

Gabriel laughed almost fake hurt at the title "That's what we are? After last night I think I deserve I better title than 'friend'" 

Sam nodded "Okay, how's 'guy I made out with that one time'?" 

"I'll take it" 

"..You know I don't regret it right?" Sam kind of randomly "In fact if you weren't avoiding me all day-

"I was not avoiding you" 

-"You would know that I wanted to ask if you'd like to hang our again..like a date" 

Gabriel heart almost stopped beating but he managed to play it off "Because you genuinely like me or because you're trying to piss off your ex girlfriend?" He questioned suspiciously; with the way he'd recently been feeling about Sam he didn’t need to be used in whatever was going on with him and Jess 

"..Because dimwit, I get these weird tingly feelings when I'm around you and you are the first person since..her- I've felt like this with" 

Gabriel's face said it all- he was scared af- had Sam fallen for him already? "Felt what way?" He asked cautiously

"Calm down..don't flatter yourself, I just mean I'm fond of you" Sam paused "..You might be a dick most of the time but, you also make me smile when I don't want to- not even Dean can do that" 

Gabriel smiled inwardly at the sentence, putting out his cigarette he said "So this date..what did you have in mind?"

Sam thought for a moment but didn't get to answers when Charlie popped up from around the corner "Dude the principles looking for you" She said 

"C'mon I just started!" Gabriel exclaimed looking to his graffiti "Not you idiot but you're bound to get in trouble for that later" 

Sam raised an eyebrow "Why is he looking for me?" Charlie shrugged "I don't know" She answered and walked away back to wherever she came from 

Sam huffed and swung his bag over his shoulder, "To be continued" He muttered reaching up he silently kissed Gabriel's cheek, following Charlie back inside and leaving Gabriel to have a mini heart attack as he continued with his art

\- 

He sat waiting in the principles office for him to arrive, trying to figure out why the heck he had been called in 

"Mr Winchester, thank you for coming" Principle -Elkins said entering the room with another student Sam recognised immediately "Sorry for the sudden call- this is Mrs Moore, she's new here and will be here for a while, I thought you could show her around" 

Jess waved a hand "Hi"

Sam blinked repeatedly, staring at the principle "Why?" 

"You seem to fit in here so well- you don't mind do you?" Sam huffed a strained laugh, trying hard to come up with a excuse "Well-, um...I" He stuttered; he really did not want to spend the rest of his school day showing his cheater ex girlfriend around 

Fuck 

"..Sure"

\- 

"These are the bathrooms" Sam pointed lazily to 3 doors that sat beside each other "Girls is on the left and boys is on the right and after half the schools -including mine- protests in the middle we have gender neutral" 

"Sam" 

He ignored her and kept walking, "This is the janitors closet though m most students go in there to fuck-so you can use it to give blowjobs to your side dudes- since you get down on your knees for anyone" 

"Sam!" 

Sam shut his eyes and pinched the bridge of his nose, turning around "What?" 

"Can you look at me?" 

"No" He deadpaned; he could not belive he was spending the end of his day showing Jess around when he could be doing literally anything else 

"Please I'm sorry about what happened between us-" 

Sam scoffed a loud laugh "'What happend between us?'- you cheated on me!" 

"I'll meet you guys in the car I'm just gonna get Sam" Gabriel waved off Cas and Dean and jogged over to his locker when he caught sight of Sam yelling at some blonde girl 

Jess 

"Hey Sam- are you ready to go?" He stood beside him looking down Jess as he saved his friend "Me Dean and Cas are going to the mall, maybe we can talk about that date you mentioned earlier?" 

Jess squinted annoyed at him "Who are you?" 

"Gabriel Novak- and you must be Jessica, I've heard so much about you- all bad of course" 

"Yeah well were in the middle of something-" 

Sam shook his head, "No we're not, let's go Gabe" 

"You were supposed to show me around!" She yelled as he walked away "You weren't supposed to cheat on me!"

Gabriel snorted 

-

"Oh icecream!" Gabriel exclaimed as they got to the iced goods section of the store "Want some?" 

Sam walked past him to the lactose icecream aisle, he picked out cookies 'n cream "I'm lactose intolerant" 

Gabriel raised a brow "I did not know that- see we're getting to know each other" Sam smiled "Yeah, sure" 

"Why are you getting icecream anyway I thought you were a huge health nut" Sam gave a long sigh  
"I need to drown my feelings- and how better than icecream..." He grabbed another tub "I don't hate her- I want to and I feel like I should but I don't and I hate myself for it" .

"Sam that's perfectly okay-" 

Sam shook his head tiredly "No, it really isn't?, she didn't just cheat on me with random guys- she cheated on me with my bestfriend" He ran a hand through his hair "What is so wrong with me that half the time I just want to forgive her?" He muttered mostly to himself 

"There's nothing wrong with you- there's something wrong with her, for letting an okay-ish guy like you go" 

Sam gave a small laugh "Okay-ish?" 

Gabriel shrugged "Meh- maybe after a few more weeks of gettin' to know you I'll change my mind" To his surprise Sam walked over to him embracing him in a hug, he whispered into his chest "Thanks Gabe" 

Gabriel hesitantly hugged him back "..-N-no problem" 

\- 

**Notes for the Chapter:**

> This chapter was getting I'mma continue in the next one and make it mostly abt Dean and Cas because I wanna throw some Destiel in here 
> 
> Kk 
> 
> Ciao 🌈


	10. Dean's got a hot date

**Notes for the Chapter:**

> Okay this chapter is so weird and cringey- I don't even know just..read 
> 
> Also I'd like to point out that this story is set in 2017 but somethings we have now in 2019 that we didn’t then are in this year, just to clarify 
> 
> This a continuation of chapter 9

-

"Guys- flowers or no flowers?" Dean asked out of nowhere, Gabriel frowned and Sam rolled his eyes out of habit "What for?" 

"..I have a date" 

Sam was interested now "With who?" In his head he was silently praying it was Cas, "Cas- 

Yes! 

"-set me up with this girl Lisa on Halloween, and we're going on a date this weekend- and I'm kinda freakin out" Sam visibly deflated and kept walking

Gabriel pushed the trolley "Cas set you up?- like our Cas?" Dean nodded, "That dick" Gabriel muttered to himself- Cas was deflecting his feelings towards Dean by setting him up with some random chick

"So flowers or no flowers?" 

Sam sighed "How well do you know this girl?" 

Dean shrugged "We hooked up on Halloween- but I don't know..a little?"

"Then no flowers" Sam and Gabriel said at the same time, Dean frowned "Huh"

\- 

"Gabe, aren't you going to help?!" Sam yelled dragging the shopping bags into the Novak's kitchen "I am helping" Gabriel said as he lean't on the counter scrolling through his phone and eating a candy bar

"Really?- I couldn't tell" Sam bitchfaced and went to get more bags "Ugh fine" Gabe set his phone and his delicious candy down and was about to help Sam with the bags when Cas walked in 

"Yo, where are my hot cheetos?" He asked looking around the kitchen, Sam cleared his throat in obvious need for help 

Gabriel tsked at his brother forgetting that Sam was carrying tons of bags that he was supposed to help him with "Cas, Cas, Cas"

Cas gave him a weird look "Gabe, Gabe, Gabe?" He repeated "Don't try to change the subject!" Gabriel accused pointing a finger "What the hell are you talking about?" Cas questioned slightly annoyed 

"Upstairs now" Gabriel said and walked past Sam who still very much needed help, Cas frowned confused and went to follow him when he caught a glimpse of his cheetos hanging out of one of the bags Sam was holding

"Oh there it is!- thanks buddy" He grabbed the bag of chips and followed Gabe just when Sam fell to the ground with a thud "...No problem" 

\- 

"What's up with you?" Cas asked Gabriel as he jumped on his bed and pulled open his bag of chips

Gabriel mimicked him childishly "Don't play dumb" He said "You set Dean up with Lisa!" 

Cas shrugged chomping down on a hot cheeto "Yeah she's in my math class, I knew she had a thing for him so gave her his number- why do you care?" 

"Why do I care?!" Gabriel scoffed "You are so full of shit!- you have feelings for Dean so you're using Lisa to give you a reason not to make a move on him" 

"No I'm not, I was just trying to help out a friend" 

"Bullshit!-" 

Cas' expression turned dark and he was annoyed "Dude leave me alone" Gabriel sighed "Fine, you-do-you" He shrugged "But just so you know I totally ship Destiel" Castiel huffed a laugh "Shut up" 

-

"Dean can you calm down, I'm almost there" Cas told him over the phone as he walked over to the Winchester residence; forgot he was supposed help Dean get ready for his date- 'forgot'

"Hurry!- she's gonna be here in less than an hour!" He was so nervous about the date, he liked Lisa a lot and needed everything to go perfect

When Cas finally got there, he ran to Dean's room "I'm here" He panted lightly; Dean turned around and Cas immediately lost his breath agian- Dean was in a tight long sleeved army green shirt with the only two buttons at the top popped and black skinny jeans that did wonders for his ass 

His hair was slightly the same as he always had but it was less messy but now it looked more kept and tame, Castiel's knees felt weak "Cas!-"

"W-what?" 

"-How do I look?" 

Like a greek god, Cas wanted to say but he stopped himself "You look good- better than you usually do" He said casually though he wanted to get down on his knees and worship every inch of the boy before him 

"Really?" Dean smiled a little; it was his first date in a while since his ex Cassie, so he had reason to be a bit nervous "You look great dude" Cas patted him on the shoulder-just like a friend would...

Dean nodded, letting himself relax a bit as he sat but ultimately he began to ramble like he did sometimes "Why am I freaking out so much?- I mean it's just a date- my first one in a while- maybe I should cancel"

"Dude"

"Yeah I could just tell her I have the flu or something-"

"Dean!" 

"What?" 

"The doorbell just rang" Cas smiled sarcastically "Go get 'em tiger" 

Dean took a deep breath and swallowed, "Okay-..jeez" He stood headed for the door, he passed Sam on his way out and the boy stared at Cas with a look full of disappointment 

Cas grimaced as Sam just shook his head disprovingly humming "What the fuck are you looking at me like that for?" 

\- 

"They are totally gay for each other and they don't even know it" Gabriel sighed; He'd been ranting about Destiel back and forth with Sam for a good 15 minutes "Hey..how close are you?" Gabriel asked referring to the fact that while they were talking Sam was on his way over 

"This close" Sam smirked knocking on Gabriel's window to signal that he was there, Gabriel scoffed and bounced up off his bed to unlock and pull up the window "Hello" Sam jumped through the window 

"Whole house is empty, what do you think we should do first?" 

Sam shrugged "Don't know, this place is pretty big- so many rooms to show me around" 

"Oh you want a tour?" Gabriel checked his watch playfully "I guess I have time" 

Sam rolled his eyes and dragged Gabriel out of the room "C'mon you dweeb" 

Gabriel led them to a room downstairs; the game room as the Novak's called it, most of their video games and things they didn't keep in their rooms stayed there

He flipped the lights on "Welcome to the Novak safe haven" 

Sam looked around; it was a big room, on the right side of the room on the walls hung guitars, electric, acoustic and colorful ukuleles that had beautiful designs, a bookshelf and a mini fridge

In the middle of the room was a black couch and in front of it was a table with a playstation and xbox hooked up to the tv that sat on a black tv stand with multiple drawers and there were string lights on the walls, on he left side of the room was a small bed with multiple emoji pillows 

"This place is.." 

"Epic?" Gabriel finished for him "I know- we all decorated this room, my mom thought it would be good for us" 

Sam's eyebrow quirked "Your mom, huh?" Gabriel didn't talk much about his parents "Yeah why?"

"You don't really talk about your parents" 

"That's because you'd have to meet them to understand them" Gabriel smirked a little, Sam shrugged 'fair enough' he thought "Who's posters are those?" He asked stepping more into the room as he pointed at the Be More Chill, WWE, Heathers, Hamilton and Dear Evan Hansen posters 

"Oh, mine and Cas'- we're kind sorta geeks..grew up watching wrestling and we like musicals" 

"Basketball?- dance?, football?- gymnastics?" Sam was pointing at medals and awards on the bookshelf Gabriel flushed just a little "Basketball, is mine I played for two years same for Cas with football" 

Sam chuckled; Gabriel was good at sports "But you're short" Sam retorted and was met with a middle finger "-and dance?" 

Gabriel rolled eyes but answered anyway "7 years, hip hop and ballet- gymnastics is Anna's shes actually really good"

"Ballet?!" 

"Okay you know what you're gonna shut up now" Gabriel said "You really know how to live a crazy life huh?"

"Crazy?- please insane is more like it, between the constant travelling- school and whatnot I have no idea how we managed to keep all this up" 

"Then why do you do it?" 

"Did-" Gabriel "I gave those things up two years ago- well except for the art and the towns annual dance-athon me, Meg and Cas- are amazing" Gabe smiled 

He shrugged focusing back to Sam's question "I don't know- a lot of shit went down before and after we moved here, I was only fourteen" 

"Shit like what?" Sam couldn't help but ask "..Well for starters, I got put on a lot of medication for this thing I do not want to talk about- I smoked, and drank" He fiddled with the ring on his finger "My grandmother died-..yeah she was awesome sweetest person in the world" He smiled faintly "She was the first person I came out too- I thought she'd be mad- but she understood- well not completely but enough to still love me..even though I wasn't blood" 

"Family doesn't end in blood" Sam blurted unintentionally "-Sorry just something my uncle said" 

"Is he dead too?"

Sam's head shook "You know- Jo's step father?"

"Whoa no way!- Bobby Singer that men fixes cars like he was born to" Gabriel sighed "I don't think he likes me very much though" 

"Why not?" 

"I maybe kinda sorta mess up my car every a few months.. it's not my fault!- I'm just usually high" 

Sam snickered- and Gabe held back and smile "Yeah whatever just follow me young padawan" 

Sam blinked "...Did you just?-" Gabriel silenced him headed out he room "Shshsh, follow me" 

-

"This is my mom's safe haven" Gabriel opened the door to an upstairs room on the third floor the only thing in the room was a white grand piano 

Sam couldn't help but gape,"You have a grand piano?" Gabriel shrugged lazily "It's her's, she used to play when she was younger but not so much now" He frowned "Why?- do you know how to play?" 

"My mom taught me when I was little but I haven't really played since then" He gestured towards the piano "Can I?" Gabriel nodded with a shrug and Sam sat down on the white chair in front of the large piano 

Sam gave a small sigh as he began and his fingers danced over the keys gracefully, Gabriel recognised the sound almost instantly, it was 'Ocean Eyes'

He watched the way Sam played so carefree and listen to how beautifully his voice rang through the house like an angel

He smiled a tiny bit at seeing Sam so relaxed and happy, he felt a strange wave of affection for the boy singing so amazingly

Sam closed his eyes, he missed this the music and the relaxation that came with it...images flashed in his mind of people, people he loved and some he lost, he just let himself feel as he played 

With one last note he spun around in the chair and faced Gabriel with a smile "..That was fun"

"That was..amazing" Gabriel corrected as he came out if his awestruck trance, he could play but not that well "Was that a genuine complement from Gabriel Novak?!" Sam gasped sarcastically and Gabriel rolled his eyes "Really?" 

The door suddenly opened and a older blonde woman entered with a bright smile on her face "Who in the world is singing so heavenly?" She asked and Gabriel's eyebrows shot up "Mom!- when did you guys get back?" 

"Just now, we would've called but we wanted to surprise you" She looked to Sam who still sat on the piano chair "You have an amazing voice" 

Sam stood up from the chair and extended his hand "Thank you ma'am" He introduced and Becky gaped dramatically turning to Gabriel "And he's polite" She exclaimed and Gabriel rolled his eyes in slight annoyance

She shook Sam's hand "I'm Becky" She smiled sweetly "Nice to meet you Becky, I'm Sam" 

"I must say I have never never seen you around my kids before- and I never forget a face, especially not one like yours" 

Sam looked at Gabriel briefly "I'm a new friend" 

Becky leaned into Gabriel and whispered "And a cute one too" 

"Mom!"

"Okay- okay, just come downstairs" She grinned "We have a surprise" 

Gabriel eyes her suspiciously "What kind of surprise?" 

-

They walked down stairs and we're met with two people, both men Sam assumed one was Gabriel's father and the other he had no clue 

But Gabriel sure did, his jaw dropped and he shook his head repeatedly "No- no-" He groaned "Not him!" 

"Hello!" The boy grinned, he seemed to be around Gabriel's age but maybe a bit older, his dad scoffed "Balthazar isn't that bad-" 

"He is horrible!" Gabriel exclaimed and rolled his eyes "Go back to England you ass"

"Oh Gabriel don't be like that" His mom said "When you said you had a surprise I didn’t know you mean't the most annoying person in the world" 

Sam snickered at that and Gabriel glared at him "Watch it moose" He turned back to his parents "I don't like it send it back" 

His dad laughed and Becky slapped his shoulder- he shut up and they walked off to the kitchen, his dad handed him a box of Macaroons on his way out "Oh c'mon you love me cousin" Balthazar cooed, he looked to Sam with a small hum "This your new bed mate?- he's cute, do you still share?" 

Sam blushed furiously and Gabriel quickly became defensive "Shut up" 

"Ohh- feisty," Balthazar teased "Where are the rest of you guys?"

"Hiding from you" Gabriel smiled sarcastically at his cousin just when the door burst open and Cas came in eyeing the four of them suspiciously "What the hell is he doing here?" 

"That's what I said!" 

"Oh come on Cas" Balthazar said and Cas rolled his eyes pulling him in for a hug- him and Balthazar actually did get along with each other and were good friends "Come, come young cousin we have much to talk about" Balthazar muttered and they walked off 

"Don't come back!" Gabriel yelled after them "British bastard" He mumbled- and turned back to Sam with a grin grabbing his hand "C'mon, let's ditch" 

Sam didn't retract his hand "And go where?" 

\- 

Okay pt 2 is in the works 

I've been procrastinating too much!-

I'd been researching Jared's character on Gilmore Girls 'Dean'- I'm not watching the show but I have watch a few scenes like when he broke up with Rory -THANK GOD- so there might be a few gilmore girls references in the next chapters

Also how did I not know that when filming season 11 Jared was in the reboot of Gilmore girls WHAT 

Anyway enough with my rambling- Ciao!


	11. (Pt2) XO

\- 

Days earlier 

Jess walked around the cafeteria of her new school, she looked lost and was a little embarrassed- out of the corner of her eye she saw someone flagging her down 

The girl looked familiar she thought and walked over to her table setting down her tray "Hey new girl-" She said "I didn't think you'd see me- sit" 

Jess slid into the seat across from her "-I'm Megan, well Meg..and you are?" 

"Jessica- Jess" She said and looked Meg over- the familiarity was nagging at her so much, "-Do you know Gabriel Novak?" She asked, maybe he'd seen her with him 

Meg nodded "Yeah, why?" 

Jess took the opportunity to find out more about Sam's new boyfriend "Just curious I've heard so much about him- but I mean from your perspective what is he like?" 

Meg shrugged "Great person, super nice, hands down best lay I've ever had" 

"You dated him?" 

Meg snorted "No- no, Gabriel isn't a guy you take home to meet the parents"

"What are we talking about?" A dark haired boy asked sitting down "Gabriel Novak" 

He perked up "Oh!- I love Gabriel Novak, I've slept with him a couple times and he did this thing with his tounge..best. fuck. of. my. life" He drooled 

Meg rolled her eyes "This is Jake" Jess blinked "So wait, you've both slept with him?" 

"Him and his brother" Meg said "Even half the school has- Gabriel is what makes Souix Falls high fun, him and his family are fuckin awesome" 

"..Do you know anything about him and Sam..uh Winchester?" She asked trying not to sound too suspicious, Meg shrugged "Not much, they went on a date a few ago but that's it- why you crushing on one of them already?" 

"Something like that" 

She spent most of her time at the school trying to find out as much as she could about Gabriel- anything to make Sam realise that Gabe wasn't good for him 

\- 

Now

"Voila!" Gabriel exclaimed widening his arms at his masterpiece; two beautiful white wings with golden tips- "You wanted to show me the crime you committed?" Sam raised his brow and stared at Gabriel who stood in between them

They were standing where they had just been the other day looking at the graffiti Gabe had been doing when Sam found him behind the school "You..are insane" Sam laughed a little 

"Thank you" Gabriel said genuinely, Sam sighed "Come on let's go inside" 

They snuck inside the school and went up to roof, where Gabriel hung out sometimes "Are you sure this is safe?" 

"Meh" Gabe shrugged, and lead them to his stash- candy, weed, smokes, cans of spray paint, Sam huffed tiredly and rolled his eyes "Gabe I don't condone your drug use"

"Calm down- they help my nerves" Gabe waved him off, and took a small hit of his bong "And let me guess you- need help with your nerves now?" 

"Exactly" Gabriel grinned- "Oh come on Samuel don't be a downer- we have one life let me live it" 

Sam shook his head- why did Gabriel always say that? "Fine but when you die of lung cancer just know I told you so" 

"Sorry I can't hear you- my mood is too high" 

"Just like you" Sam smiled "-Hey what's this?" He asked picking up a flier- something about a school dance "Oh it's just a flier for Homecoming" 

"You thinking of going?"

Gabriel shrugged "Nah, I don't know maybe" Almost as if to change subject Gabe leaned in kissing Sam "..You taste like impending death" 

"Shove it nerd" He stood dusting himself off "I got to go to the bathroom" He ruffled Sam's hair "Don't wait up kiddo" 

Sam smiled watching Gabriel go he let his fingers ghost his lips- damn he was falling- and falling hard 

-

Gabriel sighed, pulling his shirt down as he left the bathroom stall, and headed out- he heard a sound coming from one of the classrooms 

He frowned, him and Sam where the only people there right?- he ran up to the door and knocked, 

The blonde pulled her head up and Gabe instantly recognised her, "Jess?- what are you doing here?" 

She motioned to her book "I like having the place to myself-- it's the only way I can get work done"

Gabriel thought of Sam in the music room- must of been where she got that from "...Are you here alone?" She asked 

"No..uh Sam's here too" He answered and literally saw her flinch at the name "Sam huh?- are you two thing or something?"

"Wel-"

"You drag him here to screw him in every room possible?- then dump him right after?" 

Gabriel couldn't belive her, he walked into the room "Uh what?-" He scoffed "Look I don't know what you think me and Sam are doing but its certainly none of your business- as far as I know you cheated on him" 

"I'm only going to say this once" Jess stated as she stood walking to him "Back off Sam, he doesn't need you to ruin him" 

Gabriel laughed; he couldn't take her seriously, the whole situation was straight out of a movie "I'm not the one who cheated on him sweetie" 

She got a look of fury in her eyes and slapped him hard, Gabriel's head turned and he sighed rubbing a hand over his now red cheek, he went for the door

"If you'll excuse me-" Before he knew it he had been pulled down into a kiss that lasted way longer that it should've 

She was gripping and pulling at him trying to keep him from moving but he was stronger "Jess what the hell are you doing?!" Gabriel shoved her off him wiping his mouth almost immediately then Sam walked in the room after having been staring silently for a good few minutes

-She knew he was coming

"What the hell?" Sam asked incredulously "Ugh!- he kissed me!" Jess grimaced running over to Sam, "Gabe?" Sam said- he had went to see why Gabe was talking so long 

Gabriel blinked repeatedly, his breathing was speeding up "I- I have to go" He muttered running out of the door past the two

He ran until he was at the bathroom, luckily it was empty so he ran into one of the stalls and sat on the toilet trying to slow his breathing 

His head shot up when he heard the bathroom door fly open and Sam call his name "Gabriel?" He walked closer to Gabriel's stall following the sound of Gabriel's heavy breathing 

"Gabe?" 

It was a few moments before Gabriel opened the stall having calmed himself down, He smiled a little 'I'm fine' 

Sam frowned, did Gabe just use sign language? 

Gabriel realised this and his head shook "Sorry old habit- I'm fine I just freaked out for a minute" 

"I know you didn't kiss Jess, I saw from outside the door" 

"Yeah why didn’t you tell me that she was batshit crazy?" 

"Honestly I didn't know" Both of their heads turned to the door as it burst open "Sam, I can explain everything- look I'm sorry about kissing Gabriel I just really want us to talk" She begged but Sam had had enough of her lies 

He shook his head "I don't want to talk to you 'cause I don't think you wanna hear what I have to say" 

"Whatever you have to say I deserve it" 

"Yes you do- you broke me Jess..you broke my heart, over and over again- and I can't forgive that so just go back to fucking Brady" He turned to walk away when she yelled 

"So what your just going to go back to this slut you're banging!" Sam turned back anger flaring in his eyes "What?" 

Jess flinched at the anger in his eyes but continued anyway "I know about Gabriel- he's the reason you don't want to get back together with me right?- you know he sleeps with anything that walks-"

"What and you don't?- I don't care who Gabriel sleeps with, I'm not fucking him" Sam spat "And so what if he's a slut?, at least he's honest about it and not a cheater like you" He smiled sadly "No matter what everyone told me I still loved you- belived you could change- I gave you chance after chance and how do you repay me?- by sleeping with my bestfriend"

"Sam.." 

"You know, I was convinced that I loved you" 

That shattered Jess' heart  
"So what?- you hate me then?" 

"Hating you would mean I'd have to care- care about you and I don't anymore" Sam scoffed "Why can't you just grow up?- let me be happy!" 

"With him?!" 

Sam opened his mouth to yell back but he couldn't "..Ask me if I'm okay"

"What?"

Sam shrugged "You've been here for weeks and you've never once asked" 

Jess hesitated for a second but Sam was right "..Are you okay?"

Sam's head shook "No..I'm not, I...am so done, but you don't care Jess- if you cared you wouldn't be on this selfish quest to get me back" 

"Just please Jessica, if you really think you love me...never speak to me again" And with that he ran out the doors after Gabriel leaving Jess crying speechless

-

"Hey what happened back there?" Sam asked Gabriel on the walk back to his house after the whole Jess thing 

"What do you mean?" Gabriel tried to play off but Sam stopped them both from walking any further "Gabriel I know panic attack when I see one whatever it is you can tell me" 

"Seriously it's nothing, it just when Jess kissed me- like that it brought back some shitty memories that's it" He explained as they started to walk again "What memories?" Sam asked gently 

Gabriel opened his mouth to speak before closing it and reopening it "Promise you won't tell anyone?- I'm not ashamed anymore it's just not even my parents know" 

Sam nodded "Promise"

Gabriel shrugged lightly "...I was..raped when I was fourteen back at my old school in Cali" He looked away from Sam "I've had years to heal from what happened and I don't let it stop me from living my life, but when Jess kissed me so forcefully like that- I was fourteen again and he was pushing me down to my knees"

Sam didn’t even know what to say, so instead of speaking he acted, pulling Gabriel into a hug "I am so sorry Gabe" Gabriel was utterly confused to why the other boy was hugging him "This is the part where you hug me back" Sam mumbled into his chest and he slowly hugged Sam back; it was strange yet comforting 

"T-thanks" 

-

"Aww how I just missed your sarcasam Castiel" Balthazar laughed and Cas smiled at him just as he phone rang "Hold up-" He grabbed his phone out of his pocket 

"Hey Dean, how was you're date?" Balthazar watched him curiously "It was..great- I mean awkward at first yeah but I really like her Cas!" 

"That's great Dean" Cas forced a sweet voice and Balthazar noticed this "My last relationship was with my dads friends kid Leo- I really don't want to mess this up Cas"

"You won't Dean- not if you really like her" He said through gritted teeth

"I do, thanks Castiel" 

"How come I haven't heard of this 'Dean' before?" Balthazar asked when Cas hung up 

"Shut it Balth" 

"Jeez why is everyone around here so touchy?" Balthazar rolled his eyes "It's not as if you actually care for these hook ups" 

Cas went stiff for a second "..I'm not like that anymore Balthazar" 

Balthazar raised his hands   
"..Okay, whatever you say Cassie" 

-


	12. Meet the parents

**Notes for the Chapter:**

> This is the fastest I've ever updated so enjoy

Gabriel knocked on the Winchesters door, looking down at his watch- he was right on time hopefully they didn't forget 

When the door opened a man whom Gabriel had never seen before answered, "Hello" The man said and Gabriel cleared his throat "Um- are Sam and Dean here?" 

The man looked him over "And you are?" 

"..A friend?" 

"Are asking are you asking me or telling me?" The man said sternly and Gabriel gulped "T-Telling you" 

"Dad- chill, it's just Gabe" Dean said running up to the door and his dad looked Gabe over agian before walking away "Sorry about that"

"No problem" Gabriel shrugged but he still looked traumatized, Dean sighed, his dad always had that effect on people "Where's Cas?" 

"Lucky for him he's meeting us there" Gabriel muttered, "Hey Gabe" Sam smiled brightly coming out of the house he gave a kiss to Gabriel's lips, Gabriel reacted though kissing back for a moment before Sam went running down to the Impala 

Dean whistled "What was that?" Gabe blushed "Nothing shut up-, let's just go" 

\- 

They had an extra day off from school so they'd all decided to have a relaxing day hanging out by the lake 

Music was playing- Andy was swinging on a tire that was strung on a tree, some of the girls (Charlie, Jo, Meg, Ruby) had challenged Gabriel to a drinking game which he was winning at 

Dean and Lisa were making out in the water, and Sam and Cas were playing a rousing game of one touch with a football 

It was nice- peaceful- until..

"So Lisa?- is it?, you and Dean-O huh?" Gabriel started leaning back on his car, Dean gave him a look "Dude don't start" 

"No I'm just curious- I thought we had a thing you and I- I just want to know what she has that I don't" 

Dean frowned "We never had a thing" Gabriel mocked hurt "Dean Winchester you wound me" He said making Lisa chuckle and Gabe couldn't help himself "Watch out for this one Lis the mixed signals are everywhere" 

Dean rolled his eyes- and Lisa nodded "Thanks" 

Cas walked up to the group grabbing a drink from the cooler, he tried not to notice the arm Dean had around Lisa, but they shared an awkward look 

Gabriel caught on and came to his brothers rescue "Hey Dean-O you wanna see something cool?" 

"Well-"

"Great!" Gabriel popped the piece of candy he'd been rolling between his fingers in his mouth "Hey Samich over here!" He called and Sam ran over to him 

"Yeah-" Gabriel grabbed him by the neck into an open mouth kiss, the candy slipping back and forth between them- Sam moaned into it first liking the sweet green apple flavour, gripping at Gabriel's neck for more 

Their friends -especially Dean- grimaced and laughed "Okay- okay, cut it out" 

But they kept going- like fuckin' wild animals "Guys c'mon" Dean tried again and Sam raised a middle finger to him still kissing Gabriel feverishly until the candy dissolved 

Sam parted Gabriel's lips with a smile "That was.. fun" 

Castiel huffed "So is a thing now?" He gestured at the two who clung side by side "Are we honey bear?" Sam asked and Gabriel jokingly pondered the question for a second "I don't know Samshine" He said back in that same sarcastic love tone

Dean groaned while he others laughed "You guys make me sick" 

"Sorry are we offending you Dean-O?" Gabriel asked softly, "I think we've offended him Sammy" 

"I really miss when you guys hated each other- why can't you do that agian?" 

Sam and Gabriel finally laughed breaking character "Because it's too much fun" Sam chuckled watching Dean roll his eyes- he turned to his girl who had nudged him in the shoulder "I'm gonna see if the girls wanna do jello shots- you do you" She kissed him on the cheek before running off

"Oooh, adorable" Gabriel teased and Dean just flipped him off "I can't believe schools almost over.." Gabriel sighed "I have to go to college- I'm not ready for that!" 

"Gabe you're being a little dramatic" Dean said and Gabriel paled "Drama- do you know what they'd do to me at college?!" 

Cas held in a chuckle "No?" 

"Exactly, neither do I!" Gabriel exclaimed, pouting 'sadly'- "Don't give me that look Dean-O what are you gonna do huh?" 

Dean shrugged sipping his beer My dad wants me to enlist- and I've been really thinking about it- I still want to go to college but maybe after?" 

Gabriel's eyebrows shot up "Like serve?-in the army?" 

Dean nodded "Yeah our dad was a veteran- he taught us how to fight good" 

Gabriel chuckled patting Sam's back "Sam?- can fight?" Sam gave him a sarcastic smile before twisting Gabriel's arm, Gabriel yelped "You were saying?" 

He let go of Gabriel "Jeez- I don't think I ever wanna meet your parents" 

"Our mom is sweet as hell- it's our Dad you have to kinda watch out for" 

Cas quirked a brow "What do you mean watch out for?" 

"He kinda sorta has.. a gun slash knife collection" Sam rushed the last part "What?!" 

"Don't worry- he just uses them to scare people but, here are a few things you should know so that he doesn't actually use them" Sam said "Avoid direct eye contact- don't say, 'um' or 'uh'- he hates when people clam up- and until he likes you don't mention that we're are kind of going out or else he'll get out his guns and shoot you" 

"Does he know you like guys?" 

Sam shrugged "He knows we like who we like" 

"Well hate to break it to you Sammy but I've already met your dad and I'm not doing that again" 

"Shit," Sam immediately frowned "I am so sorry" 

"For what?" 

"Whatever psychological damage he's given you" Gabriel smiled, finding it nice Sam cared "-My head is fine- though he literally scared the shit out of me" 

"Of course he did" Sam sighed "It's the ex marine in him- he likes scaring the shit out of people- he's actually really nice..once you get to know him" 

"I'll bite" Cas said and Gabe gave him a look like he was crazy "More like he'll bite you" He set his drink down on the cooler, backing up "Look you guys do you but I like my life" 

"Where are you going?" Sam asked and Gabriel gave him a wink pulling off his shirt and heading for the water- Sam gasped when he caught a glimpse of Gabriel's body 

"Gabe..has tattoos?" 

Cas raised his brows "You didn't know?" Sam shook his head- how had he never seen them before? "No I did not" 

"Huh for two people so in loovve I thought you'd know everything about your 'honey bear'"

"Oh- fuck off Dean" 

-

The next day at school was pretty normal, other than the fact that it was the week before Homecoming and each day students were required to wear a different color- or style 

The first day was yellow- the group of friends obviously came prepared, Gabriel wore a soft yellow sweater under light denim overalls, a yellow beanie- with yellow vans 

Meg wore a tight long sleeved bright yellow shirt tucked into some black cargo pants, with round yellow sunglasses showing off her curly brown hair 

Charlie settled with a simple light yellow sundress, her girlfriend Jo wore a yellow shirt that said in big black letters 'Move I'm gay', with yellow camouflage pants 

Cas was wearing a yellow shirt that had a bunch of cute little bees printed all over it and his usual black denim jeans- "I like bees" He smiled

Of course the Winchesters didn't go all out, Dean with casual denim jeans a yellow denim jacket under a black shirt, and Sam went with a yellow hoddie and jeans 

"You guys are ridiculous" Sam had laughed 

-

Gabriel had wondered off from the group to take a smoke outside during lunch, he wouldn't say it aloud but he'd been trying to cut back...for Sam 

He head turned at the sound of someone walking up to him, before he looked he had assumed it was Sam but he was dead wrong

"Tsk, tsk, tsk- damn Novak" 

Gabriel scoffed stomping out his cigarette "Alistair I thought I dumped your sorry ass" Alistair smiled sickeningly, "No one dumps me Novak" 

Gabriel crossed his arms over his chest shrugging "I did" He shook his head and turned to leave when Alistair grabbed his arm pulled him back "We're not done" 

Gabriel shivered...those were the same words -he- said, it took everything he had not to punch Alistair "..Let go of me Alistair" He said as calmly as he could

Alistair grinned leaning in to whisper in Gabriel's ear "Or what, you gonna sick one of your brothers on me?" 

He was too close and Gabriel had just lost his patience, "Don't need too" He kneed Alistair in he groin and began punching him repeatedly 

When Alistair attempted to swing at him he grabbed his arm mid air and kicked him in the side, he didn't have control of his anger anymore and he didn't care, he just kept hitting until Alistair was a bloody mess on the ground "Touch me again- I dare you" 

When he turned around Sam was stood there looking as if he had seen the whole thing- Gabriel cursed himself, "Gab-"

But he just ignored Sam and ran past him 

**Notes for the Chapter:**

> Brace yourselves because things are happening!- Sabriel and Destiel wise, next chapter will hopefully be out soon.


	13. Vertigo

**Notes for the Chapter:**

> Based off the song 'Vertigo' by  
Caroline Pennell

Sam watched Gabriel run past him but didn't try to stop him, it wouldn't do anything- he looked at Alistair for a second before he headed back inside 

Gabriel had a head start so he was already gone, when he made it back to the cafeteria everyone looked at him "Find Gabriel?" 

Sam shook his head "No," He lied and Meg scoffed "Fucker skipped out on us" 

Sam didn’t really hear much after that he kind of just tuned it out, thinking about Gabriel..his fists repeatedly hitting Alistair's face- not that he didn't deserve it, he'd found the dudes hands on Gabe- his grip tightening even after Gabriel told him to let go 

But then it was like something switched in Gabriel and he just went off 

Sam remembered what Gabe had told him about- being..raped- it was horrible, Sam didn't blame Gabriel for what he did- Alistair had it coming, I mean he'd seen the kid around school and let's just say he was a dick 

After school when everyone was heading home, Sam caught up with Cas -he just couldn't help himself- he had to ask 

"Cas!-" He yelled running up to the him "Yeah?" 

"Can-..Can I ask you something about Gabriel?" 

Cas squinted his eyes at first a little confused but he nodded "Uh yeah sure" 

"Does he have anger issues?" He asked nervously and Cas immediately perked up "W-Why do you ask?" 

"I-just want to know" 

"Look Sam if Gabriel is angry, leave him alone- trust me you'll want to let him sort it out himself"

"Why?" 

"Gabriel, he's not-.." Cas huffed frustratedly "He's has bipolar" 

Sam's brows shot up "Like, bipolar disorder?" 

Cas nodded "He never liked taking his meds, they make him feel bad- hell I don't even know if he's on them right now" He frowned "If he's having trouble his anger will be worse and he doesn't like to talk about it" 

"I found him..earlier he was.."

Cas glared "He was what?" 

"Punching Alistair- but he deserved it" Sam tried to justify, "Sam- I know you just want to help him but-" 

"I know- I know but Cas..it's Gabe" He had listened carefully but he wasn't scared, Gabriel would never hurt him- Gabriel trusted him "..I'm gonna talk to him" 

-

Sam knocked on Gabriel's bedroom door, he decided not to go through the window as not to spook Gabriel 

"You can come in Sam I'm not armed" 

Sam twisted the nob and took a step into the room "How did you know it was me?" He asked closing the door

Gabriel shrugged lazily "Lucky guess" Sam looked him over; he had changed- now in some shorts but he kept on the yellow sweater, his bruised hand was now bandaged up 

His hair was messier than usual and he was leaning on the wall, with a glass in hand- was he drunk?- "Are you okay?" Sam asked gently taking Gabriel's state into account, but Gabriel just smiled sarcastically pushing off the wall "Sure" He sighed "...Sorry about earlier, I probably scared the shit out of you"

Sam shook his head "No you didn't it's fine Gabe" He said truthfully- Gabriel could never scare him

"Yes I did and no it's not I was terrifying" He muttered into his glass "I have slight anger issues..I've been handling it, but I guess I just kinda snapped" 

"Gabe seriously its okay, I get it" Sam nodded lightly and Gabriel set down his glass raising his brow, he said walking up to Sam "Look me in the eye and tell me you're not terrified of me?" 

Sam stepped closer to him tucking a strand of hair behind Gabriel's ear, Sam stared him in the eyes taking in the beautiful honey color "I'm not" 

"..Then you're crazy" 

Sam smiled nodding "Then I'm crazy" Gabriel took Sam's hand gratefully, he leaned in close to whisper against Sam's lips "Thank you" Sam paused for just a second then placed a hand on the back of Gabriel's neck "Is this okay?" He asked quietly and Gabriel gulped nodding as Sam leaned in for a soft kiss 

"Sam.." 

Sam's head shook lightly in between another kiss- he just couldn't help himself "..It doesn't have to mean anything" Gabriel hesitated "..what if I want it too?" He almost couldn't believe his own words

Sam was surprised, he let out a shaky breath "Then it can" Gabriel stared into Sam's eyes looking for anything that would stop him from saying what he was about to, but he didn't find anything 

Letting go of Sam he sat down on his bed "I like you Sam, I like you alot" Sam sat with him "Can we just leave it at that?" Gabe asked 

Sam nodded and kissed at Gabe's jaw "Yeah, we can" He kissed Gabriel's swollen lips "Because I happen to like you a lot too Gabriel" He climed on top Gabriel and leaned in for a deepened kiss

Sam moaned at the friction -the feel of their crotches rubbing together- he lifted his hoodie up over his head throwing it wherever, Gabriel kissed him agian but paused against his lips "You sure?" 

"I'm sure" 

\- 

Dean was staring up at his wall thinking hard about his girlfriend -not in that way you pervs- he liked Lisa of course, she was amazing, funny, sweet and nice- she was... great 

But Cas was..he was something else, Cas was adorable- he was cute, and funny- extremely emo- but still..so Cas,- but he couldn't- he shouldn't be thinking about Cas like that they were bestfriend's, they could never be more right?

"Stop thinking so hard" Dean's head snapped up to see Michael "-I'm not.." 

Michael snorted "Sure, okay" He sighed "Something wrong with your girlfriend?"

"No..more like.." God how could he even explain it?, "I think I'm in love with Cas" 

Michael frowned "The emo kid?- you're in love with him?- what about your girlfriend?" 

"I-..I don't know" Dean huffed and stood up "No more talking- I need a drink" It was the Winchesters way- drown your feelings in alcohol until they eventually go away

"I'll join" Michael seconded "-Oh and by the way where's Sam?"

Dean waved him off "-Probably sharing love filled looks with Gabe" 

Michael frowned- Gabriel Novak- Lucifer's younger brother, and..Sam?- "Their together?"

"Honestly I don't know- you'll have to ask Sam he's the one making faces at Gabe" 

-

Sam pulled up his pants and sat on down grabbing for his shirt "Aww don't cover up" Gabriel whined from behind Sam on the bed 

Sam looked up from behind him, "Take a picture it'll last longer" Gabriel chuckled and sat up moving behind so he directly behind Sam, kissing his neck Sam leaned into the touch 

"Do you really have to go?" 

Sam paused; he didn’t want to but he probably should, he definitely did not regret his time with Gabriel but he..had to think, he bent down to continue tying his shoes "I don't want to but I.. should- besides it's a school night, Dean and Michael are probably worried sick"

Gabriel scratched at his messy bed hair "M'kay" He yawned "..See you later?"

Sam smiled finally turning around, kissing Gabriel quickly "Definitely" 

-

Sam got home at around 8:37 pm, him and Gabriel had slept for awhile- I guess your first time can do that to you 

Sam couldn't help but smile at the recent memories of Gabriel's gentle hands on him- god it was..something 

When he got back Michael was asleep on the couch and Dean was snoring on the other one

He huffed and sat down "Wake up you idiots!" 

Michael groaned tiredly and woke but Dean just tossed and stayed asleep snoring even louder 

Michael sat up, "..Sam?- where the hell have you been?- you didn't even call we were worried sick" 

Sam looked around, there was junk food everywhere and at least 5 beer bottles on he table- 'yeah worried sick' "I was at a friends" He answered- technically it wasn't a lie, Gabriel was a friend 

"A friend huh?" Michael muttered suspiciously "And what did you do with said friend?" 

Sam grimaced slightly and rolled his eyes; he didn’t really want to talk about it "What is this 20 questions?" 

Michael chuckled "No it's more like I'm your brother and I care about you" 

Sam paused hesitating, he looked at Dean to make sure he was still asleep "..-I had sex" He smiled shyly 

"Oh.."

"-With Gabriel" 

"Oh wow- that's.." Michael cleared his throat awkwardly "Was he like your first guy or?..." 

"-Yeah, I mean..going that far" He whispered shyly "But that's not-..I'm feeling things" 

Michael snickered queitly  
"You like this boy?" 

Sam stayed silent, Michael went pale "Oh my god- you love him?!" 

"Shssh!" Sam shushed him, pointing to Dean- he didn't need his brother to know he had slept with and was in love with his bestfriend

Sam sighed "..I thought that I had been in love before like with Jess but this- with Gabriel..I've never felt like this before"

Michael smiled sadly "That's because you never loved Jess- you never bonded with her like you did with Gabe" 

"Yeah..maybe" He looked at Dean again "Don't tell Dean- Gabe is like his bestfriend- and I don't need him finding out" 

"Promise lil brother" 

\- 

"So did you and Sam fight?" Cas finally asked after Gabriel had headed down into the kitchen for some water

"Huh?" 

"He went to talk to you" Cas said gently watching for Gabriel's reaction' but he didn't get angry, Gabriel pursed his lips slightly, nodding "Yeah I know" 

"What happend?- you guys were up there for a while"

Gabriel shrugged "He came to check on me..we talked and then.."

"Then what?" 

"..We had sex" He whispered, not caring that Cas' eyes were boring into him "You did what?!"

"-It just happened okay"

Cas blinked repeatedly trying to process, he had so many questions but he settled with- "So what?- you're done with him now?-" 

Gabriel rolled his eyes "Fuck - that challenge thing okay- Sam isn't a one and done, he's..something else" 

"You have feelings for him" 

"Yeah no shit Sherlock" Gabe retorted "Don't tell Dean- he can't know yet" 

"Fine..just promise me you won't hurt Sam" 

"I won't" He promised- meaning it, Gabriel smiled thankfully, he sighed "-So what about you?"

"What about me?"

"Oh you know, the whole Dean-Lisa love triangle" 

"Shut up-- there's no love triangle, I'm happy for him" Cas muttered- not believing a word of what he had said 

"I told you about me and Sam- now it's your turn" 

Cas shrugged "Technically I never agreed to say anything" He sighed at Gabriel's -Sam- bitchface "This has nothing to do with you Gabe so just leave it alone" 

Gabriel huffed annoyed with his idiot of a brother "Come on Cas just admit it!- admit how much you hate that Dean and Lisa are together" 

"Gabe for the last time-I don't hate it- why would I hate it?, I'm the one who set them up in the first place!" 

"Because you're trying to push away your feelings- and act like they're not there" Gabriel frowned- he was genuinely confused "Why are you doing that?"

"You're doing the exact same thing with Sam" 

"That's different I have my reasons and you know it Cas- so why the hell are you doing it?"

Cas huffed- fuck it "Because I made a mistake!..Dean shouldn't be with Lisa he should be with me" 

Gabriel blinked, he already knew it but to hear Cas say it.. "...Feel better?

"No" 

-

Dean stood outside the coffee shop before taking a shaky breath and walking in and sitting down next to Lisa 

He'd spent the entire school day staring at Cas- he'd made the decision to call it quits with Lisa- and give it a chance with Cas 

He knew it was a reach but still- he couldn’t pine over Cas and date Lisa at the same time, his parents taught him better

She smiled sweetly when he sat down, making the guilt stir "Hey Dean what did you want to see me about?" 

"Okay" He took a deep breath "Lisa I like you a lot and you are an amazing girl and these past 2 weeks have been great but I just-.. I think I'm in love with someone else" 

She blinked, and Dean thought she was gearing up for a slap but she just gave a sad smile "It's Cas isn't it?" He was about to protest when she cut him off "I see they way you guys stare at each other and it's not the way best friends should" She sighed "I completely understand Dean, you deserve to be happy even if it's not with me, so go get your guy" 

"Really?"

"Yes!" She nodded with a smile "I'll be fine- just promise me one thing?"

Dean nodded almost immediately "Yeah sure what is it?" 

"Don't find some bullshit reason to not tell Cas how you feel- because I know you'll do that, just tell him straight up okay?" 

He blushed a little knowing she was right "Okay" He agreed "Are you sure you're okay?- I'll totally understand if you mad- I kind of led you on- but I swear I wasn't using you, I actually only figured out my feelings recently-" 

"Dean!" Lisa chuckled softly "I'm fine- to be honest I've kinda been crushing on someone else too" 

He frowned- "What?- who?"

"Meg.." She flushed "I know- I know, it's stupid-" 

"No-no I totally get it" He said, as shitty as it might sound it made him feel a little better about being in love with Cas "I can give you her number if you want?" 

"Seriously?- I would love that!" 

-

**Notes for the Chapter:**

> Wow another fast update?! 
> 
> Also- things are getting steamy between Sam and Gabe huh?- and no I did not intentionally avoid Sabriel smut- it is coming up- k? patience 
> 
> And yes- Gabriel has bipolar disorder- and most of his actions are loosely based on Ian Gallagher from the show Shameless who is also bipolar 
> 
> I just wanted to show that- bipolar disorder- or disorders in general, or being raped are real things and should not be ignored at all, even I was skeptical at first 
> 
> Ps. I may or may not have stolen that Cas line 'Dean shouldn't be with Lisa he should be with me' from How I met your mother 
> 
> Anyways Ciao🌈 have a great day/afternoon/night 
> 
> -


	14. You Belong With Me

**Notes for the Chapter:**

> Based off the song 'You Belong With Me' by Taylor Swift

-

2013 /flashback to a fourteen year old Gabriel/

His principle gave him a stern look "Mr Novak we don't approve of sexual acts on school grounds- you know this" 

Gabe nodded "Yes I do- I just don't care" He smirked mischievously at the Principle just when the door opened and Lucifer walked in 

"Finally- Mr Novak-"

Lucifer sat down "Please- call me Lucifer" He cast a side glance at Gabriel "What did he do now?" 

"Your brother as done some fairly crazy things his time here at our school but this one your father cannot let fly by"

Gabriel rolled his eyes, "Jeez you make it sound so bad- we were having fun!" 

"Your brother was caught..kissing another boy- on our school grounds" 

Gabe's eyes widened- he didn't think that his principle would mention the fact that it was another boy, the color drained from his face and he lost his smirk- he barley even heard the rest of what his principle and Lucifer were saying- all he got was -'three day suspension'-

On their drive back home Lucifer spoke "So..another boy huh?" 

Gabriel went stiff, Lucifer noticed this "I'm not gonna judge you promise-..are you gay?" 

"No" 

"Okay then- you wanna tell me what that was about?-you've been acting out more lately than usual" 

"I don't want to talk about it" 

Lucifer pursed his lips "Okay then..what if I tell you a secret of my own?" 

Gabriel couldn't resist "..What?" Lucifer smiled a bit "..I like boys" 

"You're gay?!"

Luci nodded "Yep" 

"Do mom and dad know?" 

"Yes.." 

"Why haven't you told anyone?- you know we wouldn't judge you" 

"..I could say the say the same thing to you too Gabe" 

Gabe huffed- he guessed that was fair "..I'm not gay- okay I still like girls"

"-So you're bisexual?" 

Gabe shook his head "I- I don't really care who I kiss, you know?- as long as I like them- it's not just limited to boys and girls" He frowned looking out of the window "I don't know it's probably stupid" 

"No it's not-..I think you're pansexual" 

Gabriel turned his head back to look at Lucifer "What's that?" 

"It's a new thing- it's kinda like being bi- but instead of being restricted to just girls and boys you love people regardless of their gender"

Damn. Gabe thought smiling, he wasn't some weirdo "Thanks Luci" He muttered and thought for a moment deciding whether to tell his brother or not "..What if it's more than just who I like- but also who I am?"

Lucifer frowned "What do you mean?" 

"What if I'm not always a boy?- sometimes I'm a girl..?" 

"Gabr- are you trans like Cas?" 

"No- Cas is a boy, I'm only sometimes a boy- or sometimes a girl or maybe I'm neither" He tried to explain "It's really more about how I'm feeling" 

Lucifer nodded processing this new information "So what are you right now?" 

Gabe raised his hand showing Lucifer a green and pink bracelet "Neither slash girl- my pronouns are they/them/she/her, mostly they/them though I'm having an off day" 

"I made these bracelets, blue is he/him, pink is she/her, purple is she/him and green is neither so they/them" 

Lucifer looked impressed "Huh-smart...but I can't keep calling you Gabriel now can I?" 

Gabe nodded "I've been thinking about that, Gabriel for my masculine days, Gabe for neither but I can't figure out a feminine name so I just use Gabe" 

"...How about... Gabby?" 

Gabe gasped "That's perfect!" They smiled "Thanks for being so cool about me"

"Anytime" Lucifer smiled back "Just if you're gonna make out with someone at school don't get caught"

-

Now

"Whatcha doing?" Sam asked joining Gabriel on the bed, Gabe shrugged closing his laptop "Just watching Rory and Dean scenes from Gilmore girls" He squinted his eyes "-You know you look a lot like Dean"

Crap "No I don't" 

"Yeah you do- I mean the hair- the height the annoying yet adorable puppy eyes- only difference is that you're nicer" Gabriel sighed, the side of his face leaning on his palm "Do you have a twin I don't know about?"

Sam pursed his lips "Nope no-..I just don't see it" He hated being mistaken for that character- Gabriel frowned looking him over, Sam seemed extremely embarrassed and flustered so he dropped the subject 

"Anywho- what doing are you here?- come for another impromptu session of vigorous sex?" Gabriel said jokingly and rubbed his shoulder up against Sam 

Sam laughed- "Shut up," He pushed Gabriel's shoulder "No- you asshat..I just wanted to know if you're free?" 

Gabriel blinked "I was watching scenes from Gilmore Girls of course I'm free" 

Sam rolled his eyes "Well in that case..there's a date we never went on..." 

"Are about to take me on date?!" Gabriel swooned "My answer is yes!- but beware I never put out on the second date...unless"

"Shut up" Sam huffed, Gabriel was all smiles until his phone rang, he didn't recognise the number but he answered it anyway "Hello?" 

He frowned sucking in his lip "Yes this is him" Gabriel sighed and nodded "Yup I'll be right there"

"What?" 

Gabriel stood taking his car keys from the table "My idiot brother got himself in trouble" Sam frowned "Which one?" 

"Alfie" He looked at Sam apologetically "You don't mind me postponing our date to deal with this right?" 

Sam shook his head "Not at all" Gabriel smiled "Great," He extended his arm "Let's go"

-

Cas was in his room sulking about Dean again but at least he wasn't alone, he gave gentle scratches to his beloved cat "You love me right Misha?" The cat purred under Cas' touch making the boy smile "Yeah you do" 

"-You talking to your cat again Novak?" 

Cas' head snapped up "Dean?"

Dean smirked "The one and only" He stepped into the room "Gabriel has officially baled on me- so I came to see what my other bestie was up too"

Cas shrugged a little awkwardly "Just hanging with Misha.." 

"Then it's a good thing I started taking antihistamines"

"You what?- why?" 

"I am very much allergic to cats, but you had one so.." 

Castiel's heart melted- Dean did that for him? "What's your deal with the furball anyway?"

" -Oh, I've had Mish since I was four, my parents got him for him after I came out, he was just a kitty then" Cas smiled thinking of the memory, "Oh," Dean cleared his throat "So..video games?'"

\- 

"I don't get it why is Alfie at school it's Saturday?" Sam asked when the stepped out of the car, Gabriel shrugged "Some freshman thing- sucks for him"

When they got to the principles office Alfie was sat at the principles desk, arms folded over his chest looking pissed, "Mr. Novak- and you must be.." Mr. Walker trailed off looking at Sam

"-My boyfriend Sam," Gabriel said so easily it made Sam smile a little "And please Mr.Novak is my father call me Gabriel" Gabriel glared at his brother who sat silently on the chair "What did he do?" 

Mr. Walker cleared his throat "He decided to cut class and was caught in the janitors closet" 

Gabriel raised his brow lazily, he just wanted to ground Alfie and be done with it "...Doing?"

"..Well-" 

Alfie huffed and rolled his eyes "I was kissing a girl what's the big deal?" Sam frowned at him- he'd met Alfie a couple times, he was a nice and quiet kid- it was strange to see him at so different

Gabriel chuckled "The big deal is if you're going to do it don't get caught" His expression changed at pointed looks from both the principle and Sam, "Look- he's fourteen- you know kids these days exploring their sexuality" He turned to Alfie "But skipping class man?- you know you can't do that, grounded 2 days- we'll hash out the deets when we get home" 

Alfies eyes widened "Oh- screw this," He stood up and stormed out, Ganriel sucked in a long breath, "...Kids am I right?"

-

When they got home Alfie ran right stairs to his bedroom, "What's wrong with Alfie?" Anna asked watching her brother go

"Hormones" Gabriel said bluntly "Please promise me you'll never turn into him- you guys were supposed to be good ones"

Anna shrugged "I'll try" That actually made Gabriel smile "Thanks little sis" 

"Gabriel- come on I think you should give him a break" Sam asked gently thinking of Alfie- he was worse when he was fourteen "He'll get a break when he stops being pissy" 

"Fine- I'll wait in your room" 

Gabriel opened Alfies door, "Hand it over" He said and Alfie sighed "Come on Gabe" 

"You can talk or you give me the xbox, choose" Alfie rolled his eyes and un plugged the console "Fuck you" He snarled, and Gabriel shrugged it off Alfie had never swore at him but there's always firsts "I love you too bro" 

He closed the door and got to his room placing the game on his table, Sam looked up from Gabriel's bed "You know I kinda dig dad Gabriel" Sam chuckled softly and Gabriel rolled his eyes "Shuddup" 

Sam smiled "Seriously you're great with kids- a little harsh but..", Gabriel scoffed; they were his siblings, when Lucifer left it was his turn to step up "Maybe, but I'll never have them"

"Really?" 

"I don't know..maybe if I thought about it enough" He sighed leaning on the counter "I mean, I've dealt with those brats for 3 years now- how the hell did Lucifer do it- you know Hanna once bit me when I took her game from her 'cause she wouldn't go to bed- just last week Anna bitchslapped me because I wouldn't let her have a sleepover with her friends- I bitch slap I don't get bitchslapped!" 

Sam held back a snicker, Gabe flipped him off "Yeah laugh it up Winchester"

Sam went to check the time on his phone when he realised that it wasn't in his pocket "Shit- I'll be right back I think I left my phone downstairs" He muttered and ran out the door

He headed down the hallway back to the stairs when he saw Alfie sitting quietly in his room thinking hard, he couldn't resist so he knocked on the open door

Alfie wiped his eyes immediately- had he been crying? "Hello?" 

Sam came in "Hey- is everything okay?- I just noticed you seemed a little upset" 

Alfie nodded "Yeah no I am fine- Gabriel's just a dick sometimes" 

"At least he loves you" 

"Yeah yeah- seriously though I'm fine"

Sam didn't belive that for a second; Alfie reminded him of him when he was fourteen- there were so many things he kept from the people who cared Jess had to push it out of him, back then they were just friends 

"Bull" He said "C'mon what's up?- is it about your xbox?, 'cause you know if I ask I'm sure Gabe will give back" 

"No- it's something else" Alfie hesitated for a second "..I think I'm gay" 

Not what Sam was expecting, but okay.., he was getting a scared vibe from Alfie it was like the way he said it he was almost ashamed "..You know that's okay right?" 

"Yeah I do- and if I came out I'd just be one more kid in the pool of gay that is my family..but it's not about that" Alfie shook his head "I was kissing that girl as a sort of experiment- she's my friend and she offered- I just feel like I don't know who- or what I am, and I've been trying so hard to figure it out-"

"But you've been getting nowhere?" Sam finished for him, "I get it I really do" He muttered; when he realised that he was bi- he had no idea what to do, he was stuck between who people thought he was and his real self 

"I also know that you usually start, questioning yourself and- feeling these things when you like someone" Alfie went crimson almost immediately, a red blush washed over his freckled cheeks, Sam smiled "What's his name?" 

"..Andrew- Andy" 

Sam frowned- Andy? "Wait Gallagher?" 

"Yeah I know, having a crush on your brothers friend- how cliché" 

"Not exactly, I think it's sweet" Sam smiled a little "Have you...?" 

Alfie got what he was trying to say and his eyes blew wide "God no- he doesn't even know that I like him like that" 

Gabriel smiled watching his- boyfriend and brother talk some more about Andy; he'd gotten impatient and went to find Sam, that's when he had saw them talking 

God he didn't even know Alfie felt that way, but Sam.. was helping him understand it- why did he have to be so perfect? 

"Look Alfie- long story short, you really shouldn't try so hard to put yourself in a box, just be a person-it doesn't matter who you like" 

"Thanks Sam- I really hope Gabriel doesn't fuck things up with you, you're alright" 

Gabriel rolled his eyes, he smiled once more wider than before, he made his way back to his bedroom to wait for Sam 

-

"Dean!" Cas exclaimed annoyedly bumping the other boy on the shoulder; they were playing Mario Kart and Dean was admittedly kicking his ass 

"Come on don't be a sore looser Cas" Dean laughed as he hit 3rd place trumping Cas' 6th 

"You're cheating!- I don't know how but you are!" They both laughed as their thumbs kept pressing buttons, both of them trying to beat the other 

And then Cas got a bullet

And he won 

Dean's jaw dropped "How in the hell did you-" 

Cas shrugged laughing so hard he had to wipe away a tear "Come on Dean don't be a sore looser" He mocked and Dean was about to pounce on him when Cas gasped at the song that started playing 

It was Taylor Swifts 'You Belong With Me' 

He jumped up and grabbed the nearest hair brush and began to sing and dance crazily to the song while Dean watched amused

"You're on the phone with your girlfriend she's upset she's going off about something that you said 'cause she doesn't get your humor like I do!" He sang as he danced with the hair brush "I'm in my room it's a typical Tuesday night I'm listening to the kind of music she doesn't like and she'll never get your story like I doooooo"

Cas pulled at his pants "'Cause she wears short skirts" And his top "I wear t-shirts, she's cheer captain and I'm on the bleachers, dreaming bought the day when you wake up and find that what you're looking for has been here the whole time!- if you could see that I'm the one who understand you been here all along so why can't you seeeee!, you belong with meeee, you belong with me" 

Dean chuckled as he watched Cas sing along to the song and smiled at his kind of good dance moves, and then he felt it something in his chest it was like his heart skipped at beat, he didn't even feel like this with Lisa or anyone for that matter but he knew that it was love for the dancing blue eyed emo in front of him

"Ah!-Cas!" And then before he knew it Cas had taken his hand and pulled him up off the couch for the end of the song and twirled like a Disney Princess in his arms letting the rest of the song play out on it's own 

Cas twirled back into Dean's arms and just as the song ended suddenly their faces were so close, so close that Dean could feel the air that Cas was panting into his face 

So close that with out realising it he had leaned in and suddenly they were kissing, Cas' hands cupped his faces and they continued in short soft kisses for only a few seconds before Cas pulled away backing up from Dean because he didn't trust himself to be too close to the boy 

He wiped his mouth "You- you have a girlfriend" Dean shook his head "I don't have a girlfriend- not anymore at least" 

"What?"

Dean sat down on the bed "I broke up with her last week, I was going to tell you today- I just didn't know" 

Cas blinked not sure how to respond; he felt oddly happy that Dean was now single but it's not like it mattered because they were just friends...just friends "..How'd she take it?" He cleared his throat 

"Honestly she took it way better than I expected" Cas raised his brow curiously "But why did you break up with her?"

Dean gave him a look "I think you already know the answer" but Cas didn't..until he did "Because of me" 

"I've always had this insane crush on you Cas- I mean Lisa was great and I really liked her but she wasn't you..she was never going to be you" He sighed "I- I love you Cas, I love everything about you- I mean-" He huffed a laugh "Man, I know you're my bestfriend but I- I want to be more than that"

He stared at his feet for a few seconds before saying "I know, it's a shitty way to feel about your bestfriend" 

Cas shook his head "No it's not" He walked over to Dean "Not if he feels the same way" He smiled and kissed the confused look off of Dean's face "I love you too" He whispered against Dean's lips "Cas.." Dean breathed

Cas just couldn't help himself, he trailed kisses down Dean's neck and sucked a hickey to his neck, Dean threw back his head and moaned softly 

Cas' began to unbuckle Dean's jeans rubbing him through his boxers, Dean whimpered when Cas pulled out his length, he licked up Dean's cock before he swallowed him down to the hilt 

"Oh- shit Cas-" Dean bit his lip to suppress the moans, his hand fell to Cas' hair gently pushing it back to see more of Castiel's face- to see his lips wrapped around his dick

"Fuck, Cas you're beautiful" He groaned dipping his head back, Cas mouth was heaven- oh his tounge licked just the right way making Dean yelp in surprise 

Cas hummed softly around Dean, and Dean was done- he held back a loud groan as he came in Cas' damp and wet mouth, Cas swallowed his release and came off with as satisfying 'pop'

He tucked Dean back into his jeans and with a smile kissed his cheek, "Damn Cas" Dean laughed and kissed Cas on the lips "..Just...damn"

-

**Notes for the Chapter:**

> The perfect way to end a chapter with Destiel smut, 💙💙💚💚
> 
> Another extra long chapter at 3152 words, damn I just can't help myself 
> 
> And that Gilmore Girls reference?- 😂- I'd just been watching Dean and Rory scenes and thought it'd be funny if someone said Sam looked like him- I don't actually watch the show
> 
> Ps. Alfie's coming out 'thing' is basically forshadowing his relationship with Adam in the sequel- yes there will be a long and detailed sequel 
> 
> Anywho!- Ciao for now 🌈


	15. Promposal

-

It was late into the night when Gabriel woke up for the fifth time, he really couldn't sleep- sighing heavily he rolled over taking his phone off the nightstand 

To Meg💀: You up?

He texted, desperately needing someone to talk to

From Meg💀: Yeah, why aren't you asleep?

To Meg💀: Why are you awake?

From Meg💀: ...Touché

Gabriel looked up at his phones time, 2:08 am 

To Meg 💀: Can I come over?

From Meg💀: Sure 

-

"Hi" Gabriel said climbing into her room from the window, She looked at him "So- what's on your mind at 2 am Gabe?" 

Gabriel sighed and sat on her purple desk chair "I need some advice..relationship advice" 

Meg grinned "Ooh do tell" She rolled over onto her stomach, head resting on her palm "..Me and Sam had sex- and I really like him but I'm not really good with romantic gestures 'like at all- but I just want to show Sam that..us it isn't going away" 

Meg smiled "Aww you l-" Gabriel grimaced, stopping her "Okay no- don't use the L word"

"Lesbian?"

He rolled his eyes "The other l word"

"..Lesbians?" She teased again and Gabriel huffed "Love! Meg- don't use that L word" 

"Why- why is it so hard for you to admit that you love him?" 

"..Because it just is okay!- are you gonna help me or not?" 

Meg sighed "..Well have you asked him out to Homecoming yet?" 

Gabe frowned "I'm supposed to ask him to Homecoming?" 

"Yes!- you emotionally constipated idiot" She rolled her eyes sighing "I wonder how you even survive without me sometimes" 

-

It was around 3 am when Sam woke to music playing from outside his window- he groaned loudly dragging him self up- who the hell was playing Heat of The Moment at 3 fucking am that loudly!

Sam pulled up his window and stared down at the assailant who held a boombox over their head- Gabriel, he looked down at his..boyfriend?- annoyedly "What in the hell are you doing Gabe?- it's freezing out there!" 

"I'm being cliché for you!" Gabriel exclaimed and Sam held back a smile which Gabriel noticed "At 3am in the fucking morning?- don't you sleep?" 

Gabriel shook his head "No" He replied casually, Sam rolled his eyes- Gabriel was really lucky that his dad hadn't woken up- or Dean "Okay, why- are you being 'cliché for me'?" He quoted 

Gabriel smirked, setting down the boombox "Because I have a question for you Samich" Sam raised a brow "What is it?" 

"Will you Sammoose Winchester, accompany me Gabriel Novak to Homecoming?" 

Sam paled immediately turning white "Wh-what?" He stuttered embarrassingly "I said!- will you go to Homecoming with me- you know as my date?" 

Sam was still in a state of total shock, not responding for a few minutes "If you don't give me an answer soon I'm gonna turn up the boombox" 

Sam grimaced at the thought "..If I say yes will you fuck off and let me sleep?" He asked trying not to smile at the thought of him and Gabriel going to Homecoming together 

Gabriel chuckled with a small grin that made Sam's stomach turn upside down, "Yes" Gabriel nodded 

"Then yes Gabe- I will go with you" 

"As my date?" 

Sam sighed with a nod "As your date"

~

Sam was particularly happy in the morning despite -the fact that he was woken up at 3 am-, all he could think about was Gabriel asking him to Homecoming 

He knew he was acting stupid- like a teenage girl with her first crush but, the butterflies in his stomach wouldn't stop fluttering! 

"Why are you so happy?- it's creeping me out" Dean finally said as Sam was making his breakfast, Sam shrugged with a smile as he poured his almond milk over his bowl of cheerios, "Gabriel asked me to Homecoming- and I said yes" 

"Wait- back up, you and Gabriel are actually dating?" 

Sam nodded lightly "I guess,- I don't really know, but I don't want to push either"

Dean frowned, he really needed to hang out with Gabriel more "Huh, well- I was thinking about asking Cas but I don't know if that's his thing" Sam paled and Dean smiled proudly "Oh yeah, did I forget to mention that I'm dating Cas? - and it's...awesome" 

"No way- I thought you'd end up marrying Lisa and having three kids with her before you realised you were in love with each other!" 

Dean scoffed "We weren't that obvious" 

Sam laughed "Oh please!" He pretended to be Cas "'Hello Dean'" and then Dean "..C-Cas'" He chuckled "-not to mention the constant eye fucking, like do that in your own time" 

Dean rolled his eyes "We do not eye fuck" Sam nodded taking a spoon full of cereal "Yeah you're right you just mentally undress each other in public" 

Dean scoffed "Yeah, okay" He cleared his throat "Not to be..annoying or whatever- but..did you have sex with him?" 

Sam choked on his cheerios "Dean- what?!" 

"-Just did you?"

"Yeah..we did a couple days ago" Sam swallowed "Are you mad?" 

Dean shook his head- "No I'm..just- you did use protection right-"

Sam cringed badly "Yes!- oh my god Dean!" He exclaimed desperately wishing that Dean would stop speaking 

"I'm just saying- you know- we don't need a baby around here and god knows what stds Gabe probably has-"

"Nope- no were not having this conversation" Sam slung his bag over his shoulder leaving his food he was out the door before Dean couldn't get another word in 

~

"So who are you bringing to Homecoming?- if you're even going?" Charlie asked curiously, as they walked the halls "Yeah I'm going..I asked Sam"

Charlie frowned sadly "Aww I'm sorry"

"Why?"

Charlie shrugged "Well I assume he said no" Gabriel rolled his eyes "He yes"

"Oh- sorry for him" She then beamed "Wait!- omg!- this is perfect we can all go together now!- you Sam, me and Jo, Meg and Lisa, Dean and Cas-"

"-Wait Meg and Lisa?- Dean and Cas?!" Gabriel gaped "When did that happen?!" 

"You're kidding me?- Destiel is totally a thing now- Cas told me everything" 

"And by everything you mean?" 

Charlie shrugged lightly "Dean broke up with Lisa and grew a pair- he finally confessed his undying love for Cas he got a blowjob out of it" 

Gabriel laughed "No- way, Sam would love this" Charlie frowned "..Speaking of..how did you get Sam to say yes anyway?- as far as I know he wouldn't bone you with a hundred condoms" 

Gabriel scoffed smirking slightly "Actually we just needed one" 

Charlie slammed her locker shut "...You and Sam..slept together?!- when where- how?-" 

"Woah calm down Granger- I'm not discussing our sex life with you" 

But Charlie's grin just grew "You guys have a sex life?" 

"Okay!- topic change" Gabe quickly said "Homecoming- we need outfit ideas!" 

"Fine I'm allowing this change- but only because this is important- but don't think I'm dropping it!" 

"Yeah- yeah I know" 

-

Sam was doing some reading when he heard an all too familiar voice at his door "You know, I don't think I've ever been in your room before" Gabriel said walking into Sam's bedroom, Sam looked up from the book he was reading on his bed

"Gabe?" 

Gabriel smirked, "Sup cutie" He winked "You're wearing my hoodie" He pointed out and Sam looked down at himself- Sam rolled his eyes in annoyance but his red cheeks told another story "..I didn't have anything else to wear"

"Riiigght"

Sam sighed,"What do you want?"

Gabriel faked offence "That's no way to greet your lover!" Sam sighed, standing up he wrapped his hands around Gabriel's neck and kissed him, Sam smiled pulling away "..Better?"

Gabe couldn't help but blush a little "Much" He smiled and kissed Sam again, sloppy but gentle- Sam kissed back hard melting into Gabriel's touch "..Sam might wanna-..stop before this gets too heated" Gabriel warned in between kisses 

Sam grinned slightly and kissed at Gabe's neck "What if I don't want to stop?" 

"..I'm..good with that" 

...

"Hello?- Sam?" Cas frowned looking around the room when the bathroom door opened and Sam and Gabriel emerged from the room looking dishevelled with smiles playing on their faces 

Gabriel smirked "You really weren't kidding when you said you give great hea- hey Cas!..when did you get here?" His brother frowned at him

"What were you guys doing?" He raised a brow at their messy hair, Sam wiped his mouth with the back of his hand "Nothing" 

Gabriel nodded "Yup..nothing" Cas rolled his eyes "Whatever- look where is Dean?- I've been trying to call him but I think his phones off" Sam shrugged sitting down the bed he looked at Gabe

Gabriel grinned remembering the two had recently coupled "I don't know bro you tell me?" 

"Ugh, who told you?"

"So it is true!" Gabe exclaimed "Congrats- I thought you'd never get your head outta your ass" Cas sighed "Have you seen Dean or not?"

Gabe shook his head "Nope might wanna check the shop" Cas huffed "Great" He rolled his eyes and on his way out he looked back at the two and said "Oh and by the way Gabe- your fly is open" 

Gabe snorted and Sam hit him with a pillow "Ow!- jeez I'm sorry!"

-

"Hey Bobby is Dean here?" Cas as the owner and Bobby nodded "Yeah kid he's in the back" 

Cas smiled at the man and with a quick 'thank you' he was heading to the back of the shop to see Dean 

Dean was cleaning his dirty hands with a rag when he saw Cas coming towards him "Hey angel" He smiled, "What's up- I'm not late for something am I?" 

Cas shook his head, cheeks red from the angelic nickname "No" Dean rasied a brow "Then what's up?" 

"..What do you think of Homecoming? I wanted to ask if you wanted to go..but if you think that it's stupid we can do something else-" 

"Whoa- Cas- only kinda of getting half of what you said" Dean chuckled lightly "I don't think it's stupid" 

"So you wanna go?..with me?"

Dean shrugged, a smile playing on his lips "You're my boyfriend, who else would I go with?"

Castle blushed hard, Dean kissed his cheek "I'm finishing up wanna go grab some lunch?" Cas nodded "Yeah..I would like that" 

-


	16. Homecoming

**Summary for the Chapter:**

> Homecoming!

  
It was the night before Homecoming when Sam was gifted with a box at his door

It was sitting there when him and Dean got back from the Novak's; they were celebrating Dean's epic football win 

Sam tiredly picked up the box and they entered the house "What's in the box?" Dean asked like he was just seeing it for the first time, Sam shrugged "Don't know" 

He looked at the velvet blue box and frowned, he set it down on the table and Dean stared at him waiting for Sam to do something "-Well open it!" 

Sam rolled his eyes but nonetheless began to open the box, he gasped a little seeing that a nice and probably expensive deep blue suit sat inside "Holy shit" Dean breathed "There's a note" 

Sam blinked, he picked up the note and unfolded it 'Can't wait to see you in this' -Richard ;)

Dean grimaced "Who's Richard?" Sam was struggling to keep in a giggle at the inside joke "No one" He muttered "I'm gonna go now" He said hurriedly and took with him the box 

Dean shook his head disprovingly "You are so weird"

\- 

"Oh my god Gabe hurry up!" Charlie screeched for the hundredth time, banging on his door Gabe rolled his eyes "You can't rush perfection Charlie!"

He set his lip gloss down and turned around and looked into his long mirror, he had dyed his hair back to honey blonde and was sporting a black and bright orange flannel styled blazer over white long sleeved shirt that was tucked into pants of the same orange and black color 

He fluffed his locks and appreciated his light make up one more time before he finally opened the door "Fina-fucking-ly!" Charlie exclaimed hearing his footsteps as he came down the stairs 

She herself was in a light red burgundy off the shoulder lace tulle short dress with a fluffy bottom and her hair was in a nice bun with a few front strands down in her face- she even wore small gold coloured earings 

Cas who was also waiting for Gabe had also put in effort; he was clean of peircings and his hair was styled sexy and messy- just like he knew Dean liked, he was wearing a white dress shirt untucked, ripped jeans and a green tie that resembled the color of Dean's eyes 

Charlie blinked "Woah you really spared no expense" 

Gabriel grinned "If that's your way of saying I look hot as hell, then thank you" He smiled and came down the stairs with a huff "So where's the booze?" 

Cas rolled his eyes "Gabe- no" 

Gabriel shrugged "What?- I'm not going to a highschool prom sober" He said looking for a good bottle of his dad's alcohol, Charlie tsked "I'm with Gabe- gimme"

Gabriel smiled proudly and handed her the bottle, she took a big swig and both boys chuckled when she sputtered a little "Slow down Charles," He took the bottle from her and took a drink

As the two passed the bottle Cas' phone rang and he answered with a disappointed sigh "Hello Sam?" 

"Has Gabe tried to back out yet?" 

"No not yet- but considering his current activities you might want him to"

"Oh god- what is he doing?"

Cas shrugged "Oh him and Charlie are just getting drunk no big"

"That's just great" 

Cas chuckled at Sam's defeated tone "How's it going over there?" 

-

Sam, Dean and Jo were still at the Winchester residence

Sam excitedly wore the suit that Gabriel gave him and Dean wore the same as Cas did except his tie was the blue of his boyfriend's eyes

Their only hang up was Jo who was over obsessing about her outfit "Jo I swear to god if you don't get out of there I will break the goddamned door down" 

"Shut up Dean!" Jo yelled at him from the bathroom and Sam snickered at the two, still on the phone "Why is Dean yelling?" Cas asked 

"Oh- Jo is just taking too much time to get ready and Dean has a short fuse" 

"Mary could you help me zip up?!" Jo asked, Mary stood and headed to the bathroom "Of course dear" 

"Dean Cas wants you to calm down" Sam said, Dean huffed "I am calm" 

"Let me guess?- he says he's calm?"

"Very" And then the bathroom door opened, Mary stepped out first with a bright smile on her face and then Jo appeared in a beautiful long satin white dress that had a cleavage showing v neck and her hair was beautifully rope braided across her head

Dean breathed "Woah, you look..like a girl" Jo immediately flipped him off, and Sam gave her a smile "You look beautiful Jo" 

"Thanks" Jo smiled shyly smoothing down her dress "..I just hope Charlie thinks so too" 

-

Sam stood before Gabriel and his boyfriend looked him over with a smile "You look amazing" Gabe said and kissing Sam slow and sweet, he parted from Sam with a grin "Shall we?" 

They all arrived at Homecoming looking dashing as ever, it was more than fun- especially for Gabriel because all he did was complain on the way there about how cheesy highschool dances were 

But for Sam he tried, he even slowdaced though if you asked him he'd never admit it 

Charlie almost passed out when she saw how beautiful Jo looked and Cas and Dean couldn't keep their hands off of each other all night- even Lisa and Meg showed up together

The night was going perfectly until..

Cas and Sam were standing alone at the back of the party watching the teens dance and drink, Cas turned to Sam with a fond smile "You know I still can't believe that you and Gabriel are actually going out" 

"Why?" 

Cas shrugged "Because Gabe said 'getting' you was a challenge..you know tricking you into bed- I told him it was stupid but Gabe just never gives up"

"A challenge?" Sam asked his voice breaking and eyes watering as he listened, and Cas nodded "Yeah- well at first anyways-" 

He wasn't listening to rest of what Cas was saying, the only thing he had processed was that Gabriel was using him- the whole thing was game to him

Sam cleared his throat "Will you excuse me?" He said not waiting for an answer before he ran outside of the school and all the way to the back finally stopping at to fall back on the wall

His breathing heavy as tears fell, he ran a hand through his hair the same word falling from his mouth over and over agian 

Idiot 

Idiot 

Idiot! 

"Sam?!" He heard Gabriel yell as he turned the corner to find Sam crying "Sam what happened are you okay?, Cas said you ran out-" He tried to get closer but Sam wouldn't let him "Don't- don't you dare" Sam's voice was angry now, still pained but angry "This- us it was all a challenge!?, I was just another one of your conquests huh is that it?" 

Gabriel cursed under his breath "Fuck Cas" He muttered "Look Sam I can explain everything-"

"Was any of it even real?- Sam let out a pain cry when Gabriel stood silent not knowing what to say "You piece of shit!" He yelled "I trusted you- I opened up to you!- I told you things that I've never told anyone- and all of it was just you trying to get laid!" 

"Sam-"

"God I feel so stupid!" Sam breathed a loud laugh "I actually thought you, had feelings... for me?" He shrugged turning to leave "Goodbye Richard, I never want to see you again"

When Sam was gone Gabe basically lost it "Stupid- stupid- stupid!" Gabriel muttered repeatedly hitting himself in the head "Gabe- Gabe what's wrong?" It was Dean's voice "Dude, what's wrong?" 

"Sam..-Sam just broke up with me" 

~~~~


	17. Sex, Violence, Smoking &- Love?!

**Notes for the Chapter:**

> Smut warning!

Luckily when Sam got home there wasn't anyone there to ask questions so he just ran up to his room, making sure to lock the door behind him not wanting to be disturbed at all 

He sighed and looked for some more comfortable clothes to change into

After discarding his tux, he got a pair of plaid pajama pants and he found himself grabbing the hoodie Gabriel had given him a while back when he'd been sick

He didn't want to smile but the hoodie smelt so much like Gabriel but it didn't change anything Gabe still lied to him

He sighed and fell onto the small bean bag in the corner, he felt like an idiot, of course Gabriel never really had feelings for him, I mean why would he? 

And the worst part is that Sam still has feelings for him, and no matter how hard he tries they aren't going away anytime soon 

He picked up his ukulele and began to strum it lightly, he did this sometimes when he needed to calm himself, he was trying to find the right tune and when he did he started to play as memories of him and Gabriel ran through his head like an old movie

\- 

"Oh my god Gabe stoooppp" Sam whined tiredly, it was 10 am on a Saturday and Gabriel had climed in through his window (because apparently that's their thing) and has been trying to get him to hang out ever since 

Gabriel threw another skittle at him "Come on Sammy, we only have one life to live so let's live it!"

But Sam just groaned "Gabriel it's Saturday, let me sleep" 

"Sorry Samshine no can do"

Sam huffed, he ultimately decided that Gabriel wasn't going to stop until he got up so he managed to pick himself up and- sneeze!

He sneezed again causing his hair to go everywhere, and then suddenly he felt his head start to throb in pain "Ugh, Gabe I think I'm sick" He sat back down on his bed wrapping his shaking arms around himself 

Gabriel frowned and stopped throwing skittles "Yeah, you look sick too"

Sam rolled his eyes "Thanks" 

"That's not what I-" He sighed and pulled off his hoodie "What are you doing?" Sam asked suspiciously 

Gabriel chuckled "Calm down I'm just giving you my hoodie, you look cold" 

"Gabriel I don't need your- achu!" Sam sneezed again "Okay maybe I do" He muttered quietly taking the soft light pink hoodie from Gabriel's hands and putting on over his white t-shirt 

He smiled hugging the hoodie close, "So warm" it was like he was hugging a cloud, a cloud that smelled like candy- and Gabriel and he kind of liked it, but he wasn't going to say that aloud 

Gabriel found himslef staring but he chose not to comment on how cute Sam looked in his hoodie with his blush red nose but instead to take care of his friend "Welp, since you're sick, it looks like I'll have to take care of you" 

Sam shook his head "Gabe you don't have to do that really" 

Gabriel grinned slightly "It's no problem Sam, just think of me as your guardian archangel" 

\- 

"Okay it's on" Gabriel nodded turning the camera 'round to face him "April 22nd 2016- the squirrels have taken over and mankind as we know it is over" 

Sam scoffed "Gabriel what the hell are you doing with my camera?" Gabriel started to film Sam "Making memories!- I mean I want the future weirdos to know that we- us cool people did cool stuff" 

Sam smiled sarcastically and stared at the camera "Gabriel can you put the damn thing down, we're supposed to be going to Dean's stupid football game" He muttered fitting on his shoe 

Gabriel smiled "And we are going to cheer the hell out of it" Sam rolled his eyes "Sometimes I wonder why we're even friends" 

"Are you saying you want us to be boyfriends?- 'cause I'm down with that"

Sam flipped him and the camera off and left the room "Come on we're gonna be late" 

Gabriel sighed flipping the camera over to himself "Kids.." 

"I heard that!" Sam yelled "And your like 2 years older than me!" 

Gabriel blushed giving a happy chuckle "Aww Sam Winchester, you might not know it yet..but someday you're gonna fall in love me.."

"Gabriel if you're not here in 2 seconds I'm not letting you bring the camera!" 

Gabriel laughed "Welp future hubby's calling" 

\- 

-May 2nd-

"Happy birthday loser-you are officially 16!" 

"I'm seventeen dumbass" 

"Oh I could've sworn you were 12" 

"Fuck you"

"Wow birthday boy's gotta tounge, why don't you use it-" 

"Nope- no, don't even finish that thought" Sam put his hands up in disgust "Are you seriously filming this?" He asked noticing the camera 

"It's your birthday Sammy!- how could I not!" 

Sam chuckled nodded "Yeah, sorry I forgot- you want to make memories for some dumb reason" 

Gabriel got both of them in the frame as he scooted closer to Sam on the bed "Because, I want you to remember why you fell in love with me" 

Sam shook his head confused "But I'm not in love you" 

"Not yet" Gabriel sung "Anywho back to this birthday thing, I being the amazing, great, and awesome person I am-

Sam snorted 

"Got you a gift" 

"Gabe seriously you shouldn't have"

"It's in my nature Sammy-birthdays are just my thing"

Cas opened the door "Guys were going to The Roaadhouse now so hurry your assess up" He smiled at Sam "Happy Birthday loser" 

Sam scoffed; they were so alike "Seriously what is with you guys?" 

Gabriel turned to camera to Cas filming his confused face "He hates birthdays" He whispered not so quitely and Cas gasped dramatically "Birthday hater!" 

"I don't hate birthdays!" 

Gabriel tsked "Sure sounds like you do Samich" 

"I hate both of you" 

-

Sam's head turned and he stared at his bookshelf, Gabriel had gotten him the entire Percy Jackson Book Series because he once mentioned that he'd been interested in getting into the fandom 

He let himself give a faint smile as he continued to reminisce 

-

Gabriel hovered on top of Sam as they kissed, Gabriel's hand slowly fell to the bottom corner of Sam's shirt and it stayed there as he waited for a nod of consent that came almost instantly 

Sam sat up and Gabriel lifted his shirt his head tossing it elsewhere, Sam paused and stared making Gabe frown "What?" 

Sam placed his hands on Gabriel's shoulders twisting him around "You never told me you had tattoos" He said running his fingers over the tattoo on Gabriel's upper left back

It was a feather tattoo that cut off into tiny birds at the top- it was beautiful 

Gabriel scoffed "Well you weren't so eager to see me take my shirt off when we first met" 

"Why'd you get it?" 

Gabriel turned back around to face Sam "To embrace the worst moments of my life..help me let go" He smiled "Now could we get back to.." 

Sam rolled his eyes and kissed Gabe softly, Gabriel pulled down Sam's pants and came back up to rejoin their lips as his hand slipped into Sam's boxers 

Sam gasped into Gabe's mouth "Good?" Gabriel asked and Sam nodded "Good- definitely good" 

He chuckled softly, rubbing him to full hardness, while Sam writhed and moaned under him, he moved down Sam's body and pulled off his boxers- he licked up Sam's cock deep throating him "Fuck- Gabriel" 

Sam dug his hands into Gabriel's hair, bucking his hips into Gabriel's mouth at the pleasure, Gabe went faster and Sam moaned loudly feeling his climax near 

He'd had blowjobs from guys before but none like this- jesus Gabriel's mouth was a velvety heaven

With one last whimper Sam came into Gabriel's mouth feeling Gabe swallow him down "Gabriel" Sam was sure of it, he wanted more, he pulled Gabriel up into a hard but controlled kiss "Someone's eager" 

"Fuck me Gabe"

Gabriel didn't know why but he hesitated "Sure?" Sam moaned against his lips "100 percent" Gabriel nodded and kissed Sam "Has anyone ever told you how beautiful you are?" He whispered not able to help himself

Sam blushed "No" He knows it's stupid but the few times him and Jess had sex it was all about her

"That's a shame because you really are" Gabriel's words made Sam shiver "You use that line with all the guys?" He sassed quietly "Not unless I mean it, so no" 

He pressed their naked bodies together making Sam whine "Mmm" Gabriel smirked "Calm down, I'm not teasing" 

Sam layed back down, Gabe kissed his neck "Have you ever..?" 

"No- but I give great head though" Sam countered with humor even though he was nevervous "I'll have to take you up on that sometime" 

He lubed his fingers using the hand that wasn't bandaged up, and started with one entering Sam, the boy gasped but didn't protest he began to drag his finger in and out- adding another when Sam nodded for more 

When he was sure that Sam was ready, he pulled his fingers out, rolling a condom over his dick and lubing it up "Ready?"

Sam rolled his eyes a little "Just do it you-nghh!" He groaned when he felt Gabriel's cock split him open, "What?" Gabriel grinned but Sam was too busy getting used to his size

He pushed himslef in completely and Sam felt the air knock out from his lungs when Gabriel brushed against his prostate "Fuck Gabe!" 

Gabriel gave a dark chuckle  
"Sorry- I'm a tease" He sped up just a little and Sam moaned loudly biting down on his lip "S-shit Gabe...kiss me"

Gabriel nodded leaning down to kiss Sam- engaging in a sloppy but passionate make out session, Gabe's thrusts were like magic each one hitting his spot harder than the last 

They were fast but Sam could tell due to Gabe's hand injury he was having some trouble, so Sam grinded his hips down to help "I want you to try and do something for me okay?" Gabriel panted into Sam's ear, "Mm?" Sam hummed 

"Close- fuck- close your eyes" 

Sam nodded letting his eyes fall closed "Take your dick- in your hand" He instructed "And jerk yourself off" 

Sam swallowed "You want me to get myself off while you're getting me off?" 

"I promise you it's going to feel great"

Sam slipped his hand between him and Gabriel's bodies to grasp his cock, jerking it slowly, focused on Gabriel, his touch- the feel of him buried deep inside Sam "Mm Gabe..fuck" Sam moaned lowly "Faster" 

Gabriel nodded and made his thrusts faster, practically abusing Sam's spot, it was like everything was hitting Sam all at once- soon his breathing quickened as the pleasure rose "Gabe!" He gasped "I'm gonna cum" With a few more slow tugs at his cock and Gabriel's merciless thrusts Sam came painting his stomach white with his cum 

Gabriel followed soon after, just from the sight of Sam's face twisted from the pleasure- 'he looked pretty fucking amazing'- Gabriel thought, just before he came filling up the condom with his release 

He gave it a few seconds before he pulled out of Sam falling bonelessly next to him on the pillow, Gabriel smirked to himself as an idea popped in his head before he rolled back on top of Sam- head positioned just before his cock, Sam frowned "Gabe- what are you- ohh" Sam whimpered softly

Gabriel was cleaning the cum from his -overly sensitive- cock, trailing up all the way to his chest taking every last bit of Sam's cum, when Sam looked down and met Gabriel's eyes he couldn't resist the urge to kiss him softly, turning the tables so that Gabriel was under him as they made out 

When they finally managed to pull away from each other, Sam rolled back next to Gabriel on the bed, and Gabriel tossed the condom

Sam took his hand and nuzzled up into his chest, he slowly fell asleep- and Gabriel just stared down at the beauty before him 

He kissed the top of Sam's head and pulled the covers up, they stayed like that sleeping peacefully till the night

-

Sam winced..he prayed that the sex had actually mean't something to him

-

Dean knocked on Gabriel's door   
"Gabriel?- it's Dean, so you wanna come out..talk to us?" 

It's been almost a week since they found out he'd stopped taking his meds, his siblings tried to talk to him but Gabe wouldn't budge

His parents had even tried themselves, and Gabriel had almost caved but decided his room was the best place to be

Only one person hadn't gone to see Gabriel and that was Sam, he knew that Gabriel didn't want to see him and yes it hurt but he had to respect Gabe's wishes no matter how much he wanted not to 

"Sam just talk to him- he's your boyfriend you have to help him!" Dean pleaded for the 3rd time this week following Sam up the stairs, "Dean I don't know what we are!- and Gabe doesn't want to see me okay?!" 

"How do you know that?" 

"I just do!- so leave me alone, he'll leave on his own" Sam slammed the door in Dean's face and threw his things on the bed

He really thought he believed what he had been saying, that Gabe didn't want to see him- and all he needed was time but he wasn't quite believing it anymore

He felt useless- why wouldn't Gabe talk to him about the things that were bothering him, he thought honesty was what they were working on in their messed up relationship 

"Fuck" He huffed and stood up grabbing his bag and pulling out his phone to send a quick text before he headed out his bedroom window 

\- 

When Gabriel heard his phone ping he picked it up, seeing a text from Sam 'I'm coming over' 

No 

Gabriel couldn't look Sam in the eye not after what happened-

He felt ashamed and more depressed then he'd ever been in his entire life, after he'd flushed his meds down the toilet his whole family was on his case and he wanted badly to talk to them but he couldn't because they'd give him that look- the look of pure pity that he had hated seeing all his life 

He was a freak and he knew it, but he couldn't have Sam look him like they did

A knock to the window snapped him out of it as Sam pulled open the window and jumped into his room 

"Sam..you shouldn't be here" 

Sam shrugged innocently   
"Yeah well..too late" He sighed defeatedly "Gabe I'm done, I've given you your space and time- and if you won't talk to your family than at least talk to me" 

Gabriel shook his head wincing   
"..I can't" He sat up cross legged on his bed still clutching his small throw pillow "Why not?" 

Gabriel didn't answer, "I know you're off your meds Gabe- I know that you're bipolar..." 

Gabriel looked down shamefully "And I don't care, you are you no matter what" 

"...You don't understand" 

"Then help me understand Gabriel- tell me I'm just here to listen, I'm not gonna judge you" 

Gabriel sighed "It's a long ass story" 

Sam smiled a little and sat down on the desk chair "My favourite kind" 

"I was 4, when I first told my parents I had a crush on a boy, my dad was happy but my mom not so much, she went all religious freak on me" He paused "A few months later, my dad skips town and leaves me with that witch until C.P.S finally got me away from her" 

"I was adopted by Chuck and Becky a little while later...back then it was just me, Cas and Luce- Lucifer and I didn't get along at all but me and Cas were bestfriend's-" He smiled a little "I was so confused when my parents told us that Cas was a boy- but still I loved him the same- we did everything together... we had fun" 

"Fast forward a few years of a great life and more siblings to annoy- I started questioning my sexuality and gender identity.. I was thirteen when..I met this guy, James he was 15 at the time we'd kiss and make out in the school janitors closet- never went further than that but one day James he just.." 

-

//FLASHBACK// (Warning graphic rape scene) 

Gabriel was walking down the halls of school heading for the entrance to where his brother would be waiting for him 

He made it to a classroom when he was grabbed and yanked in by someone, "What the hell?!" He screamed looking up he saw who it was "James-what the fuck?" 

The boy smiled "Football practice just ended you wanna mess around?" He asked, Gabe shook his head straightening out his clothes after James rinkled them "Can't my brothers gonna be here any minute" 

"C'mon" James used his signature smile- the one he used to get what he wanted, and Gabriel caved "Fine but only five minutes" 

James nodded and pressed his lips eagerly to Gabriel's, he picked the smaller boy up and placed him on one of the desks standing in between Gabriel's legs, they made out for a little while before James started to get grabby 

Gabriel noticed this and tried to get him to stop because he didn't want to go that far, but James wasn't taking the hint, he grabbed at Gabriel's jacket pulling it off as he kissed down his neck "James- stop"

But he didn't "C'mon, Novak you want this" He went to pull down his pants and Gabriel shoved him off, hopping off the table "No I don't!- I told you James no serious stuff- I'm fourteen" He grabbed his jacket off the table and went to leave the room when a strong hand pulled him back "We're not done" 

Gabriel struggled in his arms "Get off me you ass!" He exclaimed and James slapped him, he kicked Gabriel down to his knees and pulled out his dick, "I'm not sucking your dick you twat waffle" 

He slapped Gabriel again and held open his mouth shoving his dick down Gabriel's throat without warning, tears ran down Gabriel's cheeks as he gagged- the feeling hurt his throat, James was too big 

The strong footballer held him in place as he fucked Gabriel's mouth ignoring the quiet sobs and tears coming from him 

When he came he forced Gabriel to swallow, and pulled the fourteen year olds now limp body up from the ground, he held a tight grip on Gabriel as he used one arm to clear the teachers desk 

Gabriel swung- fist connecting with James' face, but that just fed his anger

He bent Gabriel over the wood and yanked down his pants- the only thing Gabriel could think was 'he's gonna rape me' 

James stuck his fingers in Gabriel's dry hole and Gabriel yelped in pain as James moved his fingers in and out trying to open him up, Gabriel didn't know how long it was before he finally pulled them out- but he knew what was coming next 

He shut his eyes to tune it out but just as he did the door James had locked was kicked open and Gabriel heard his brother Lucifer run in yelling

James had let go of him and he had slid to the floor, he clutched his knees to his chest, ignoring the pain from his ass every time he rocked back and forth 

He saw Lucifer repeatedly punching James until his face was bleeding bad, when Luci was done beating the hell out of him, he pulled Gabriel up fixing his clothes he held his little brother in his arms and carried him out to the car 

\- 

When they got home nobody was there so Lucifer took Gabe straight to his bedroom, "Luci?" Gabriel said, it was the first time he had spoken after they left the school 

"Yeah Gabe?"

"Don't tell-please don't tell" Gabriel pleaded, "Gabe you have to go to school with that monster!-" Lucifer tried not to raise his voice 

"I don't care!- please just..please don't tell" Lucifer nodded reluctantly and hugged Gabriel who cried all the tears he had been keeping in into his shirt

Lucifer wasn't letting Gabe go back to school with that son of a bitch 

End of flashback 

\- 

Sam was speechless, the fact that someone did that to Gabriel just...he wanted to know about Gabriel's past but jesus he didn't know it was that dark

"- A few days later I got back to school and James was nowhere to be seen, part of me knows that Lucifer had a hand in that- but he never told" Gabriel nodded lightly "After that we stopped fighting all the time and became actual brothers, my parents had no idea how it had happened" 

"..I still wasn't okay after the whole James thing, that time was just so shit- my grandmother died- she loved me so much- even trusted me enough to give me this" He rubbed the silver ring he always wore on his finger "Her wedding ring..she knew that I was aromatic-ish but the old woman still belived I'd find someone" 

He sighed "I really changed when I was 15, I started to smoke and drink- party and- sleep around- I lost my virginity to my two friends Luke and Jemma- they were super cool about it, and patient with me..it was nice" 

"I was diagnosed with bipolar 1 when we moved here- but like now..I wouldn't take my meds I was stubborn" He scoffed "Meg, was the one who got me to do it- she was the girl next door, we shared windows and I would sneak out to see her whenever I could, Cas dated her first- they were all hot and heavy for a while but they ultimately broke up" 

"Then me and her started hooking up- a friends with benifits thing, she didn't know everything about me but she knew enough"

He looked up at Sam "Then you Winchesters waltzed into town, and I was immediately captivated by you..I don't know how you did it but you made me feel things-things in my 18 years of life have never felt before" 

He un cluched the pillow "So that's my life..Sam, well most of it anyways- how can you possibly understand that?- no one else does" 

Sam shrugged "I can understand a little" It was his turn to open up "My parents are great but between work and me and Dean they were barley there- I was..raped too- last year- when I made the dumbass decision to go to some stupid party with a friend, He admitted "And some girl decided it be fun to drug me"

"..I think it's why Jess cheated on me so much- because I wouldn't put out anymore" 

"It wasn't your fault Sam" 

Sam nodded "..Maybe one day I'll belive that" He stood to sit next to Gabe "Gabriel, I know you're going through something tough and I'm not trying to get you to take your meds..I just want you to talk to me- tell me these things" 

"I don't know how.." 

Sam sat down next to him and took his hand "-Today was a start" Gabriel smiled and hugged him "Thanks Sam"

"No problem Gabriel-"

"Gabby" Gabriel corrected him shyly "Gabby- or Gabe, I'm still genderfluid" Sam kissed his cheek "Sorry, Gabby" 

\- 

Sam smiled.. it was the first time they had really opened up to each other- that felt real, in his heart of hearts Sam knew Gabriel hadn't lied about that one 

He set the instrument down; no- he wasn't going to be that person, him and Gabe were close and Gabriel wouldn't of hurt him intentionally

So he was gonna give him a chance- to explain, but if he didn't like what he heard?-.. then they were over 

~

**Notes for the Chapter:**

> Hey hope you guys liked this..the end is almost near so be prepared- also a quick happy birthday to Sam Winchester- thanks for being a person fictional or not- you're awesome 💕


	18. Breakup Blues

**Summary for the Chapter:**

> Sam's sad
> 
> Gabe is sad
> 
> Everyone is sad

  
Dean stared blankly at his brother when he entered Sam's room to check on him "Is that your 2nd tub of icecream?"

Sam shook his head lazily "Third" He muttered with a mouth full of chocolate chip, Dean rolled his eyes "Sammy come on!- it's been three days since at least talk to the guy- he's miserable!"

Sam looked up for a moment "Really?"

Dean nodded thinking that maybe if Sam knew how heartbroken Gabe was he'd talk to him, Sam shrugged "Good" He said and continued eating "Dean- you're my brother I thought you'd be on _my_ side" He mumbled

"I am it's just..Gabe isn't that bad of a guy- and as much as it pains me to be helping you keep him- you should _at_ _least_ hear him out"

Sam paused

So remember how he'd agreed to hear Gabe out?- he'd really tried but he was too scared so instead he just told himself that he was letting Gabe stew and freak out for some time- which was totally not the case

"..Nope"

_Dean groaned _

-

Gabriel was moping in his bedroom stuffing his face with candy- he was utterly and completely _miserable _

Cas had apologised for letting his secret slip but Gabe didn't blame him, it was his own fault- Sam was just protecting his heart- and rightfully so

His dog made a sound almost like sad bark as he stared at Gabe accusingly and Gabe stared right back "What are you looking at?"

Dickie trotted over to his clothes hamper and pulled out Sam's sock that he'd left over once from it, giving it to Gabriel, he sighed sadly, petting Dickie "I know- I know.. I miss him too"

He looked up with hope in his eyes when he heard a knock at the window it was pulled open but Dean was the one to climb through "Ugh it's you"

His friend sighed "Good to see you to"

Then Gabe realised "Shit Dean- I swear I wasn't trying to hurt Sam-"

"I know" Dean said cutting him off from his apology "I know- you wouldn't care so much if you didn’t really love my brother Gabe" He nodded "We're cool"

"Really?- you're not going to hit me?" Dean shrugged "Not unless you give me a reason to"

"..How's Sam?"

"Moping in his bedroom at stuffing his face with icecream.."

Gabriel winced "I really hurt him didn't I?" Dean sighed, "He just needs time"

"..yeah 'time'" Gabriel scoffed "Cas still feels bad..he shouldn't" Dean frowned he hadn't spoken to Cas in awhile except for on their phones "Is he here?" Gabe nodded "Probably"

~

Dean knocked on Cas' bedroom, "Who is it?"

"Dean"

There was a short pause "..Come in" Dean opened the door, and found Cas sitting at his desk on his laptop "..Hey- you okay?"

"Yeah I'm fine" Cas sighed "How's 'Sabriel' doing?"

"Sam still refuses to speak to Gabe"

Cas slumped in his chair "..Yeah and it's all my fault"

"No it isn't"

"-If I'd just kept my mouth shut- god I am such a lazy drunk"

"Cas come on, you can't think like that- you told Gabe not to do it he _chose_ to ignore you"

Dean's eyes fell to Cas' desk "..Who are those people?" Dean asked looking at a picture frame, there were two adults in the picture a man a woman smiling

Cas shrugged "My parents" Dean frowned raising a brow "Biological parents" Cas elaborated "..They died when I was a baby..-car crash- they were friends with Chuck and Becky- who happen to be my god parents"

He stared at the picture "I don't talk about them much..I mean I barley even knew them" Cas said "Becky says they really loved me"

"I'm sure they did Cas" Dean said noticing that Cas seemed a little skeptical of his mom's words, Cas nodded "Yeah" He shook it off "So shall we?"

"Uh-where are we going?"

Cas grabbed his jacket with a huff "Anywhere but here"

~

"You dun fucked up"

Gabriel looked up from his bed, "Alfie?- aren't you supposed to be in school?"

Alfie rolled his eyes "It's summer break" He looked his brother over stepping into the room, "Cas told me what happened"

"Ugh- of course he did"

"You know I liked Sam- now you're gonna go back to Meg," Alfie shivered for affect "She scares me"

"She scares everyone" Gabe retorted "And I haven't lost Sam- I'm just giving him some space..and time"

Alfie sighed "Look Gabe I know that you're..emotionally constipated or whatever- but Sam brings out the best in you"

"The best in me?"

"He makes you a better person- and keeps you in check..and you probably won't admit it but c'mon Gabe- the guy makes you happy"

Gabe toyed with his lip, "..Okay yoda..what do you suggest I do?"

Alfie looked around the room grimacing at the candy wrappers everywhere "Clean yourself up and get your guy back"

Alfie left and about an hour later Gabriel was in the middle of taking his younger brothers advice and cleaning up his room when his phone started to ring

He turned around to grab it answering immediately "Hey, mom- aren't you supposed to be on a flight?"

_"Not yet- we have some time" _

_"Is y__ou're better half there?"_ She asked teasingly and Gabriel raised a confused brow "Huh?" so she alaborated _"Sam, that nice boy with the fantasic voice?" _

Gabriel pouted "Oh..he's..I don't know"

_"What's wrong?"_

"I may have messed up big time with Sam"

_"Well what did you do?" _She asked gently, Gabriel scoffed "I can't tell you 'cause if I do you'd come back here just to hit me upside the head for being a complete idiot"

_"Possibly but tell me anyways"_ Gabriel sighed "I manipulated his feelings- for my own personal gain" He rushed his words a little "I didn't mean to- but then it got serious and he found out about what I did and I'm not really sure I can fix it"

There was a little silence before Becky spoke_ "..You know me and your father try to do the best we can to understand you kids and for the most part we do- but..you Gabriel- you're something else, you have a big heart and this amazing personality and we could never understand why you didn't want to share it with anyone"_ He could hear her smile_ "But after you met Sam..he changed you for the better..and if he loves you too you can fix it" _

Gabriel nodded "Yeah okay..thanks" He sighed "Have a safe flight mom"

He dumped his phone on his bed and plopped down next to it "..I can fix it"

_~_


	19. Forgive Me?

**Summary for the Chapter:**

> They talk.

  
_To Sam: 'Can we meet up?'_

_..._

_From Sam 'Where?'_

_~_

Sam took a deep breath- _he could do this, _Gabe just wanted to talk- and he could do that _talk_

I mean it's not like he wanted to make the first move anyways, he was just.._scared- _he knew the second he looked into Gabriel's eyes or Gabe spoke.. _he would fold like a piece of paper_

He checked the clock by his bedside, _5:01 am- _fuck it was early- but early was..good- yeah _good_

So against his better judgement he crawled out in the morning through his window to meet up with Gabriel

They decided to meet in the woods- well it was more like Gabriel's choice not Sam's

"Hey" Sam said when they came face to face, "Hey" Gabe said awkwardly, the atmosphere was so thick you could cut it was a knife

"Are you still mad at me?"

Sam shook his head "No.." Gabe scoffed "C'mon Sam even my dog hates me"

"He can't hate you Gabe"

"Then why does he look at me like I denied him one of his favourite treats- which I never do" He said "Seriously everyone thinks that I'm an idiot, for what I did to you"

Sam frowned "Who's everyone?" Gabe shrugged "My mom for one- yeah she misses the heck out of you- you know how hard it was to tell her it's my fault that one of the best things that has ever happened to me hates me?"

Sam ignored the way his stomach flipped at Gabe's words "I don't hate you Gabe- strongly dislike at the moment? - _yes_ but I could never hate you" Sam sighed "Look, I'm not going to be that person that won't let you explain why you did what you did- so explain"

Gabe took a deep fuckin' breath "-Yes at first it was just about getting you to fall in love with me so I could sleep with you, but then we actually got to know each other and-" He tried to find the right words "..-You're different Sam-I have never once felt this way about anyone-"

Sam avoided Gabriel's eyes "Felt what way Gabe?- because apparently I was just another conquest to you"

Gabriel shook his head "No Sam- I'm not a guy who gets these kind of feelings at all- and I have tried so hard to push them away but I couldn't because-I realised.." He sighed "I don't want to"

"Sometimes I look at you and it's like I forget how to breathe for a second- you do that to me- my make my heart hurt but it is so fucking worth it.."

"Gabe..I" He was at a loss for words, Sam thought about it for a little bit, he mulled over everything Gabriel and him had together- maybe it wasn't real at the start but it sure as hell felt real now "I..I believe you- and you might be a dick..but I guess I also forgive you"

Gabriel was kind of stunned "You- do?" Sam smiled and walked up to him "Yeah I do dumbass" He kissed Gabriel lightly pulling away they just hovered close "You taste like candy" Sam whispered and Gabriel smiled "You taste like icecream"

They both grinned momentarily before attacking each other's lips, they made their way to Gabriel's car kissing against the door before Gabe finally pushed it open, he scooted inside the backseat and Sam crawled on top of him

They made out feverishly, pawing at each other, Gabriel pulled off Sam's jacket and then his shirt, Sam helped him take his off and they parted to get their pants off

Sam straddled Gabriel's waist, he was bent down kissing Gabe hard, Gabe reached into Sam's boxers and pulled the waist band down, he took their cocks in his hand and began to jerk them fast, he didn't really know what he was doing but he knew it felt good

Sam buried his head in Gabe's neck sucking purple marks to the skin as Gabriel worked their lengths expertly, he grinded his hips down making more delicious friction and their cocks slid together perfectly

He worked his thumb over both of their slits, smearing precum all over their throbbing heads, Sam's hips jerked and Sam thrusted into Gabriel's fist, every part of his body was humming with electricity and they'd only had sex once before

Being the teenagers they were their orgasams were already nearing but Gabriel wasn't slowing his hand movements, he was panting hard and Sam gave a long moan into his neck and the painted their stomachs white with cum

Sam took a moment before rolling off of Gabriel and to lay squished beside him, one word falling from his mouth

_"Fuck"_

~

_Earlier_

"Cas what are we doing?"

Cas shook his head "I just want to walk" He said quietly "Is that okay?" He asked and Dean nodded "Yeah of course"

It was quiet for a while, the only sounds were the trees swaying and they stayed in the comfortable silence before a sigh from Cas broke it

"Have you ever been in love before Dean?" Castiel asked shocking Dean out of the silence "Before me?"

Dean nodded hesitantly "Yeah..I have..once, uh.. last year" He sighed "His name was Leo, he was a family friend who just got out of college"

"College-?"

Dean rolled his eyes "_Yes _he was twenty two, but he was also my first time with a guy- and I.. I miss him sometimes" He admitted, and then grimaced slightly at himself "Sorry if that's weird-"

"No no- I get it" Cas insisted, "..What happened between you two?"

Dean shrugged "We broke up before the move, but it wasn't-.. I..we had fun, we had a great time together we both knew it wasn't forever but that doesn't stop us from being friends"

"That's nice..I've never been in love before you..me and Meg didn't work out and all my other relationships were purely sexual" Cas said "I don't even know what love is..nobody does really"

"Well love is love right?- it's that overwhelming feeling of happiness you get when you're with the one you want to always be with" Dean tried to explain, "How do you feel when you're with me?" He asked stepping in front of Castiel

Cas took a moment "...Content..like I found something I didn't even know was possible" Dean smiled "I guess the best relationships are the ones you never see coming"

Cas smiled too "Yeah I guess" He turned around to face Dean "Thanks for listening..I usually ramble about stupid things-like the meaning of life and shit"

Dean shook his head "Hey- you let me go on about all the different types of pie I like- no one has ever done that- not even Lee"

Cas bit his lip "Are you in the mood for some icecream?" He proposed and Dean rose his brow "Icecream huh?..I guess I could- I mean if I have time of course-"

Cas shoved him- annoyed with the teasing "Oh shut up- and let's go"

~

Gabriel sighed "I wish we could do this more often" Sam almost laughed "What?- have sex in the backseat of your car?"

Gabriel snorted quietly "No..I just mean-...this is nice" He smiled "Being with you"

Sam kissed his cheek "Aww you sap" Gabriel rolled his eyes "-You make me happy okay..that's not really a familiar feeling"

Sam's smaller body climed on top of him "I wanna say something okay- but I don't want you to freak out- or feel the need to say it back- I've already forgiven you"

Gabe nodded hands kind of stroking Sams thighs "I promise" Sam sighed heavily ".._I_\- Sam Winchester, love you Gabriel Novak" He announced playfully "I love you so fucking much"

"..Sam"

"Remember- you don't have to say it back not until you're ready- I just..I want you to know it's how I feel about you .."

"I don't..."

"If you say- 'deserve to be loved' I will prove you wrong in so many ways- you're amazing Gabe"

"-I love you too" Gabe blurted and Sam looked semi shocked but Gabriel just shrugged sheepishly "Just wanted you to know"

"Well.." Sam beamed "Thanks for letting me know" Gabriel faced Sam "Hey..when did you know?"

"..That I loved you?" Gabriel nodded, and Sam thought about it "..I guess the first time we had sex..whenever me and Jess were intimate like that it was _forced_ sometimes I wasn't even in the mood but I felt pressured..but with you.." He trailed off "..It made me realise that I never really loved her- just the _idea_ of her" He gave a small laugh "And look how that turned out"

He smiled at Gabriel "But hey at least I met you" Gabriel grinned "Yeah..I know, I am a gift" Sam scoffed "You're an ass"

Gabe nodded "Yes I have phenomenal ass" Sam laughed "Yes you do"

~

"So you guys are like good now?" Cas asked, seemingly not convinced after the couple had told their friends that they had patched everything up and weren't fighting anymore

Sam nodded "Yup"

Charlie raised a brow "Just like that?" Gabriel nodded "Just like that," Jo frowned "Uh, huh- and what exactly did you do to warrent this brief break up?"

Gabriel looked at Sam expectantly, thinking that Sam would answer her honestly but his boyfriend shrugged "Not important" He frowned "Aren't Meg and Lisa supposed to be here?"

Dean chuckled "Oh no- they are caught up in their _love _nest" He teased and Charlie nodded "Yeah after the dance they were on each other like white on rice- she did send me a wet tongue emoji (👅💦) the day after so they definitely hooked up, called it from day one"

Cas scoffed "No you didn't" Charlie shook her head, shoving him away "Sshh"

~

**Notes for the Chapter:**

> To be continued in next chap (last one)


	20. Leaving Souix Falls

**Notes for the Chapter:**

> Last chapter!

The following summer was awesome to say the least, they all hung out everyday doing random stupid fun things

Dean, Gabriel, Meg, Lisa and Jo flew to Califorina for a tour of Stanford as well as apartments and when they came back they were joined at the hip with their partners until their days together were almost up

"Gabriel seriously I'll be fine!" Sam assured his boyfriend for the 5th time

They had a two days left of summer and since Gabriel was heading off to college and Sam still had a year of high school left Gabriel was reluctant to leave, not wanting to part from his boyfriend even if it was just for a year

_"No, Sam seriously I'll take a year off I don't need it anyway" _Gabriel said "Yes you do Gabriel- you need to go be a college boy, I promise we'll still talk and see each other- I promise"

Gabriel huffed defeatedly _"..Fine, but I still don't like it"_

Sam chuckled on the other line "Of course you don't"

"Hey Sammy can you get off the phone with your boyfriend and help me pack now?!" Dean yelled from his bedroom, Sam rolled his eyes with a huff "Sorry- Dean needs me, I gotta go"

_"See you tomorrow?" _Gabriel asked and Sam smiled "See you tomorrow.. love you"

Sam paused for a moment wondering if Gabriel was actually going to say it back, he was hopefull seeing as Gabe had been trying to get comfortable with saying it more often, _"I love you too Samich"_

Sam smiled softly as Gabriel hung up, staring at his phone for a moment before finally putting it back in his pocket and running back upstairs into Dean's room

~

"Was that Sam?" Cas asked taping off another box, Gabriel nodded "Yep"

Cas raised a brow "Did you give it to him yet?" Gabe shook his head "No- I have to wait for the perfect moment" Cas chuckled "Wow Gabriel Novak _a_ _romantic_?- you really have changed"

Gabriel blushed furiously "Shut up" He grumbled "It's just a stupid key"

~

When Sam was done helping Dean the two went over to see their boyfriends to spend the night together

Dean stayed in Cas' room of course and Sam in Gabriel's, when Sam woke up Gabriel wasn't in bed and Dean and Cas had left the house which was empty with the exception of him and Gabe since the rest of his family weren't gonna be around for most of the day

"Gabe?"

He said with a yawn as he stalked downstairs in only his boxers and one of Gabriel's big light yellow shirts that were almost the length of his boxers, to the delicious smell of food and the sound of music

Gabriel was dancing to Panic At The Disco as he made breakfast humming softly he smiled noticing Sam coming down stairs "Morning Samshine!"

Sam chuckled softly at Gabriel "Morning to you too" He kissed Gabriel's cheek "You're happy"

Gabriel shrugged "Well I have reason too"

Sam rolled his eyes though smiling, he hopped up on the counter with a sharp breath "Fuck- my ass still hurts"

Gabriel pouted "Sorry baby- want me to kiss it better?"

Sam shook his head with a laugh "No thanks I'm good"

"Your loss" Gabriel muttered quietly as he cracked another egg

Gabriel physically melted and he couldn't stop the smile from spreading on his face, he walked over to Sam, hands gripping the counter as he leaned forward and Sam picked his head up "I love you, you know that?"

Sam smiled softly "I love you too" He muttered and Gabriel gave him a small peck on the lips

"So are you even just a little bit excited for college?" He asked Gabriel as he went back to cooking, "I guess- I mean there's a lot I have to do if I want to open my own bakery or you know create my own treat" He joked "It's kinda a dream of mine"

"That's what your doing?" Sam asked incredulously; Gabriel had never mentioned what he had wanted to do in life "That's awesome Gabe it's like a huge deal"

Gabriel chuckled "Don't get your hopes up- I still a have a long ass way to go" He sighed "But there's something else I wanna tell you" He said nervously though Sam couldn't tell; he put their plates down on the table

Sam shook his head, hopping off the counter "No wonder you cooked"

Gabriel scoffed "Yeah- well you know how I'm getting an apartment near Stanford and I'll have the whole place just to myself, I wanted to give you this" He pulled a key out of his pocket

"What is it?"

Gabriel smiled shyly "The key to my apartment, you know if you ever visit Cali you can come stay with me-" He was cut off when Sam pulled him down by his shirt and kissed him, taking the key from his hands in the process "I would love that" Sam hugged him tightly and Gabriel breathed a sigh of relief as he hugged Sam back

"I'm gonna miss you Gabe" Sam muttered sadly, "Don't say that like I'm leaving forever, I'll just be at college"

"Yeah, but what if I'm having a mid life crisis and the only fix is your cuddles?"

Gabriel chuckled "That was very specific" He looked down a noticed that Sam was actually starting to tear up- but he had to stay strong for his Sammy "Hey, come on Samich don't get soft on me now"

Sam wiped his eyes but the tears kept coming "I'm not" Gabriel kissed the top of his head "I love you Sam Winchester- always"

-

Gabriel was packing what was left in his room for college when he found the portrait he had painted of Sam and he remembered the day like it was yesterday

They were out in the woods because he had somehow convinced Sam to help him with some dumb art project- and then they got popsicles and Sam confided in him about Jessica- right before Gabriel got the bright idea to paint him

He smiled 'that was a fun day' he thought "Knock knock" Cas said walking into the room he sat down with Gabriel, Cas gasped "I remember that painting Sam tried to pretend he hated it- it was hilarious"

Gabriel couldn't even respond due to the tears that were falling down his cheeks, Cas immediately noticed his sobs "Hey- Gabe what's wrong?" He asked gently

Gabriel wiped his eyes "I'm just- I'm gonna miss him- you, Charlie- Souix Falls, I'm gonna miss all of it"

Cas shrugged "It's just one more year until me, Sam Charlie and the rest of our idiot friends join you"

Gabriel stared at the painting "I just wish I had more time with him" He sighed "I dont want to be away from him Cas"

"Yeah because you love him"

Gabriel nodded smiling "I do- so fucking much"

"Remember that talk we had the day those Winchester brothers got here and turned our whole lives upside down?"

Gabriel swallowed nodding "Yeah you were telling me off about some guy I hooked up with- classic Castiel move by the way"

Cas rolled his eyes "Anyway- you told me that love wasn't real- and I should just give up while my heart was still intact"

Gabriel scoffed "And it's a good thing you didn't take that dumbass advice" He sighed "To be honest I just didn't want to get my heart broken a billion times just to find 'the one', lucky for me I got Sam" He looked at his brother "What about Dean?- aren't you upset you're not gonna see him for a year?"

Cas nodded "Of course I am, but a little distance won't kill us"

Gabriel laughed at how nonchalant Cas sounded, swinging a arm around his brother he sighed heavily, "I'm gonna miss you little bro"

~

The morning Gabriel and Dean were leaving for their flight, Sam and Cas had spent the night with their boyfriends once again

They left for the airport early, Sam and Gabriel were saying their final goodbyes just 10 minutes before they were supposed to bored

"Okay Samshine, I have one more parting gift" He revealed a long black velvet box from behind his back handing it to Sam "Open it"

Sam eyed him suspiciously as he opened the box, it was a silver necklace with a ring attached to it; Sam gasped, he knew that ring "Gabe this is.."

"My grandmothers ring, yeah" Gabriel nodded "I thought you lost it?"

"I did, but then I found it"

"And you're giving it to me?- Gabriel you _love_ this ring"

"I do and I also love you- and my grandmother knew that I might never find love, but she said that if I ever did I should give this to them- she probably mean't propose but.." He shook his head and smiled, moving to stand behind Sam putting the necklace around his neck "You're them Samshine"

Sam chuckled "Really _Samshine?_\- that's new" Gabe pursed his lips "Oh you don't like it?- because I got tons more-"

"Nope-no Samshine is just fine" He smiled, hugging Gabriel when he came round from behind him "..You know I thought that after Jess I was gonna have the worst year ever, granted it was shaky but...I'm really glad I met you Gabe,"

"Ditto- Sammy" He kissed Sam's lips, savouring it as their last kiss for a long while "It's been a pleasure" He turned to walk off when Sam grabbed him by the arm "Hey Gabe?"

"Yeah?"

Sam smiled brighter then ever "..Challenge completed"

-

**Notes for the Chapter:**

> The following series 'Challenge Accepted College' should be out today or tomorrow

**Author's Note:**

> I have no idea where this stories going..


End file.
